Rocking S Ranch Reviews

This was a surprise trip from my boyfriend for our birthdays (both in the same week). It was not a bad drive out from Richmond and the scenery was beautiful. The ranch was not hard to find and had a really authentic vibe. Our guide Bill was my favorite part, he was hilarious and very passionate about what he does. We got to hear some really interesting stories along the trails and he took lots of great pictures for us! The ride was lots of fun, we got to go on trails, roads, and through some water so lots of variety. I would easily recommend this for friends, couples, or kids. What a great time! We will definitely be back!!

AMAZING!! Bill is fantastic, he’s very easy going and very informative. He’s loaded with dad jokes and loves talking about his daughters and their accomplishments. He is very much a proud parent! We eloped and decided we wanted to do something fun right after and figured what better way than going for a horse back ride! After three long rains of constant rain the skies finally cleared up right at our appointment time. Although it was mostly dry we had a few wet spots when going under trees where the water droplets would fall. However we loved it and it made it feel like a REAL authentic horse ride instead of one of those dull and boring ones you would get at a prestige vineyard. 10/10 would recommend and return again!!!

This was really everything we wanted out of a trail ride. Bill took my phone as we entered the wooded trail & kept taking picture of us throughout the trip which awesome. The trail itself was fun. We went up and down some pretty steep inclines & thru a stream a couple of times. Way more interesting terrain than we city folk have ridden thru on past rides.

This is just a one man operation so if you call & have to leave a message, understand that you are calling Bill's cell not some assistant, and he's either on a ride or getting the next group ready. It took a few missed connections for Bill & I to finally talk on the phone but it was worth it. Highly recommended for a fun laid back experience.

The place is a small family owned. The owner was incredibly friendly and did everything he could to make us feel comfortable and enjoy our trip. The trail he took us along was gorgeous and it was a little hilly making it fun to ride the horses up and down different inclines. He took plenty of pictures and let you know what to expect. I would recommend this place to anyone who wants to go for a little horseback riding.

We had a fabulous time horseback riding at Rocking S Ranch. The owner was friendly, funny and very professional. We did trails which wasn’t the typical flat land horseback ride. We did hills and even crossed a stream. It was our best experience so far. I highly recommend this place.

My grandsons, my friend and I had pretty much no experience riding horses. Bill was so patient, and was such a great instructor and guide. He entertained us all along the way. The boys were held pretty close at first, but by the middle of our ride they were navigating the trail on their own. Such a great confidence booster for them. I highly recommend Rocking S Ranch! This grandma loved it!

My boyfriend and I went to the Rocking S Ranch for a trail ride this weekend. We had such an amazing time with Bill and his horses. Bill is an awesome person who really took the time to get to know his guests. He made the trail ride fun and informed us of where we were going and what we were going to be doing. The trail ride was exciting and involved riding over multiple types of terrain. This activity is great for all sorts of riders! We will definitely be back!

My partner and I were looking for a quick last minute local event to enjoy around the area. Bill was more than accommodating and entertaining during our leisurely ride through the woods, over creeks, and around the property.

Bill is a pro and a heck of a nice guy. He doesn't just know horses and riding, he understands people, and makes sure they are comfortable and ready to ride. It is a really fun day out, even if you have never been on a horse before. Super fun. Thanks Bill

Me and my husband enjoyed our time with Mr. Bill ! it was definitely more than a horse riding experience. He is very knowledgeable bout the Winchester area and gave us a good recommendation for a restaurant. My favorite time was riding the horse in the water ! It was my second-time doing riding a horse and he made sure we were at waste. Thank you for this great experience!

My husband and I booked the 1.5 hour ride with Bill during our anniversary stay in Winchester this past weekend. What a fabulous time! Neither of us had any real horseback riding experience, but the horses were gentle and easy to ride. And Bill was a great guide. He gave us the necessary tips along the way and kept us laughing with jokes and stories. Not to mention all the great photos he took!

It was a great time with Bill! Very funny and beautiful trails to go on! Perfect birthday gift for anyone. Very fun for anyone who hasn’t gone riding before. Id definitely recommend giving Rocking S Ranch a call and getting a riding time setup!

Had a nice ride out with Bill in the Blue Ridge this afternoon. His horses are very gentle and well behaved, the scenery was beautiful, and I’d come back for the cowboy puns any day ;)

We had a total blast! My cousin is here from England and we really wanted to ride together. The trail ride was amazing and such a good laugh. Especially the jokes told through out! The horses were so sweet and the trail was very pretty. Would defiantly go back again! Plan to go back again soon!

If you are looking for a fun, family trail ride this is the place for you. A REAL trail ride like I remember from days-gone-by with great scenery, through multiple habitats (wetlands, meadows, thickets, pine and older growth forests). Bill and Haley were welcoming and their horses were healthy, engaged and well mannered. I forgot how much I miss riding and am so glad I chose the Rocking S! This is NOT your dreaded nose-to-tail through-the-fields ride. My teenage nephew was visiting and had never ridden before but he took to it from the start and we all had a wonderful experience. These days you have hit a homerun when your teen says "I'd do that again in a heartbeat!" A fun and memorable day with action photos to boot!

Great location and horses were very sweet. The guide took pictures for us throughout and suggested a good place to eat after we were done.

Bill was a great guide we had a blast! The horses are in great shape and are well taken care of. Would definitely recommend!

I highly recommend this Ranch for a trail ride experience that you will never forget . Bill was knowledgeable , friendly, patient and we had a perfect day ! The scenery is tranquil and the day was just perfect ❤️ Go here and you won’t be disappointed !!

Bill was super nice and we had a great ride. My daughter enjoyed his "Dad" jokes. Would definitely recommend.

The ranch was beautiful, the horses were great, and my friends and I all had a super fun time!! I greatly recommend coming here

Me and my girlfriend had a great time riding with Bill he is an awesome man. Thanks for everything Bill.

We had a great with Bill and the horses! Bill was such a lovely guide and very clear with instructions. We’re hoping to come back again in the near future! (Brooks is the sweet horse in the picture)

My wife loves trail rides. We'll go on one almost every trip we take and have high expectations. Bill helped make this one a memorable experience and didn't let us down. While entertaining you with stories and jokes he'll document your ride like no trail ride we've been on. He is knowledgeable about the area attractions, hiking and restaurants. Horses were well behaved, friendly and easy going. Definitely a fun time along the ridgelines, forest and stream. Great to meet you Bill.

Bill is an engaging and humorous conversationalist. Trails were shaded, with scenic mountain views, stream crossings, hills and wildlife. We will definitely go again to enjoy Bill's hospitality, the gorgeous views and of course - the well-mannered horses. Great value!

Had a great time .Very scenic ride .Bill took time to explain the ride and made everyone at ease . He made the people that didn’t have much experience comfortable will definitely go again

We went to have a nice trail ride, and had a great time. The owner is very kind and takes pictures throughout the ride. Both horses were well trained and good for beginners or experienced riders.

Such an amazing time at Rocking S Ranch! Bill was hilarious and a great guide. Amazing views and very well trained and beautiful horses! Definitely recommend visiting if ever in the area!!

Such a great ride with Cowboy Bill! We got to see different kinds of scenery along the way, including walking through creeks.
Warning: your face may hurt from laughter (lots of jokes) and you may learn a thing or two.

Way back in September 2019, for my birthday, I visited the ranch with a friend. We drove from Columbia, MD to Winchester, VA which was about 1.5 hours drive. The ranch was pretty easy to find. We met Billy and he was as friendly and welcoming as can be. It was my friend's first time on a horse and Billy was very patient and explained everything to perfection. The horses were beautiful and well groomed. It was a hot day (90's) but we rode through shaded areas and a stream which helped. The trail ride was fantastic! Billy kept us entertained with his corny jokes. The horses were very sweet and gentle. When we returned to the stable, Billy recommended places to eat in the area, upon our request. We wondered if the horses would get a bath since it was so hot. When I got home, there was a message from Billy letting us know that he had hosed the horses down and that they loved it.
It was a great way to spend a birthday!

I went with my girlfriend and friend for 1hr and half long ride,and Bill gave a great tour! We definitely recommend this place.
P.S. he is also a great camera man.

Neither of us had been on horseback for many years. No problem! Bill had us up and riding in no time. In less than two hours we rode on open ground, through meadows and forests, and through a stream. We had a great vacation, and this ride was really the highlight. Don't miss it!

Great experience! Highly recommend Rocking S Ranch. Bill does a great job making you feel comfortable on your horse regardless of riding experience!

Bill was wonderful...and so were our horses Brooks, Leroy & Sheena! It was a great way to spend a spring afternoon. My husband & Bill exchanged jokes along our ride, and we learned a little bit about nature & the local flora & fauna as well.

Took a wonderful ride with Cowboy Bill today. Healthy horses, beautiful views, varied terrain, and a good time all around. This family run business cares about its customers and animals. Bill made the trip even better by taking lots of photos so we could remember and share the adventure. Highly recommended.

My friend and I had a great time today at Rocking S Ranch! The horses were wonderful, and Bill was a great guide and leader. I enjoyed the water crossing and spending some time walking in the woods. What I appreciate the most was how quickly Bill got back to me after I left a message late in the afternoon and accommodated my last-minute request for a next day trail ride! I would definitely like to return.

Bill was great. My 6 year old daughter loved it. Made us feel comfortable for first timers. Great scenery, awesome views! I would highly recommend!

Absolutely an awesome experience! Bill makes it a perfect family time with his humor and patient teaching skills. As new trail riders, we were made to feel very confident about being on a horse. Our ride was a surprising adventure with a new terrain around every corner...from country roads, wooded terrain, hills, and water. We left with smiles and memories...we will be back!

Absolutely loved the trail and the area! Had an incredible time speaking with the owner, Bill, during our visit. He was friendly, patient, and quite knowledgeable, not only about horses, but about a wide variety of subjects. Super helpful and conversational! Would definitely visit again!

In response to a previous low review someone posted: This place is open, but was previously closed temporarily due to the owner having a serious, intensive surgery. He stated he has only recently recovered from said surgery and will now be working to maintain the area as he previously did.

It was a great horse riding experience on my birthday! Bill was a cool guy who provided clear instructions on how to handle horses even how to stop them from snacking on leaves on the trip. It was very nice to be able to ride on my own most of the time instead of riding on ponies. Do not get me wrong, ponies are good but riding on a real horse is a real experience! My family members also loved this experience too. As previous reviewers mentioned, Bill always make cheesy jokes. :) Thank you Bill for making a great experience for us!

I booked a trail riding session with Bill that turned out to be a super nice experience. Bill was very personable and funny and the trail ride offered a variety of terrain that made the experience that much more enjoyable and memorable. I will be back in the near future on my way down to Southern Virginia. Well done Bill!

My girlfriend booked this activity for my birthday trip to Winchester and I must say- we were not disappointed! This is a family owned operation, which makes it very special and unique! We were taken for a scenic ride in the country, and even crossed a quaint stream and ascended a large ridge. It was fun and eventful. The family that owns this is very friendly, helpful, and down to earth. They made sure to make us feel welcome to the area, having never been here before. Highly recommend!

This is one of the few ranches in the area that is open year-round. and you really can't good wrong by coming here. The owner, Bill, is a gregarious and engaging guide, who will pepper you with stories, jokes, and personal insights that will enhance your riding experience.

The ranch itself is unpretentious, and the herd is modest (only 9 horses), but the horses are good and game, and the trails are varied and pretty. In addition, Bill goes out of his way to give you great service. For my girlfriend and I, Bill generously extended our ride from the 1.5 hours we paid for to almost 2.5 hours! In addition, he took tons of pictures with my camera so that we could long remember our trail-riding experience.

Overall, if you want to ride, this is a sure bet.

We had a great time. Beautiful day, perfect weather. I highly recommend Rocking S Ranch! During this time of uncertainty, support local businesses 👍👍👍

I took my 14 year old daughter for a great ride with Rocking S Ranch today. Bill was a fantastic guide and the horses were calm but obedient. The whole ride was enjoyable with hills and stream crossings, great views, and for the most part cool covered paths.I can't wait to go back, perhaps with my wife.

Excellent place for horseback riding! Bill guides you through the ride and gives pointers on handling the horses which are the best behaved horses we have ever ridden. You get a variety of terrain and we even crossed a stream a couple times. Excellent rates too! Highly recommend if you’re staying anywhere in the area! We stayed in Harper’s Ferry and it was well worth the drive over.

My husband and I came back for our 10 year anniversary. It was just as great as I remember it. The owner makes you feel right at home. We will definitely be back.

Great ride on a hot day through cool woods, stream crossings, and a very entertaining wrangler. My 9 and 11 year old grandchildren loved it.

It was an awesome Day to go riding!.Bill is amazing & funny guy.Go show him some love and his horses

Rocking S Ranch is the best horseback riding I've ever been to! I've been to multiple horseback riding trails throughout the Virginia region and Bill at the Rocking S Ranch make your experience the absolute best!

My wife and I was visiting Hillbrook Inn to celebrate our 1st year Anniversary and I saw "Rocking S Ranch" as a good activity for us. I called to asked a few questions before our trip and Bill was absolutely friendly! I could hear his excitement and friendliness through the phone. Once we got our reservation all set up and finally met him at the ranch, it felt like I was meeting up with a friend by how welcoming and friendly Bill was. My wife, who hadn't ridden a horse before, instantly felt comfortable and was ready to get on a horse because of how welcoming BIll and his nephew Jr was.

We got to ride Leroy and Timber. Two beautiful horses. We followed behind Bill as he told us local stories, funny jokes, and asked us about ourselves. It felt like we were all friends just going out for a nice horse ride. We felt like we lived here and we were neighbors! The scenic route we took was amazing and Bill did a great job at taking amazing photos of us with our phones.

I've made this longer than it needed to be, but we absolutely loved it!

My boyfriend and I went to Rocking S Ranch on a 1.5 hour horseback riding trail. The owner and guide, Bill, was extremely personable and funny! Not only did he share stories and talk to us throughout the ride, but he was very knowledgeable about the plants and animals along the trail. If you’re visiting the area and are looking for other hidden gems in the Winchester area, Bill is very acquainted with the area and can tell you the best spots to visit!
We went as a couple’s date, but if you’re thinking about taking children, the horses are very well trained and gentle. Overall, we had an amazing experience and can’t wait to ride again! 10/10 - 5 STARS!! :)

This was so fun! Bill was great! The trails were great! This was my daughter’s first trail ride. She can’t wait to visit Rocking S ranch and Timber(her horse) again.

Bill (the owner) was so nice and made the ride extra fun. The trail was beautiful and it was well worth the money. I would definitely go back. Don’t feel discouraged if he doesn’t answer the phone right away. Keep calling and he always gets back when he can. He’s a very busy man and can only do so much. Very happy with the experience and would be happy to go again😁

Bill was an amazing host on our ride today. My boyfriend and I had no prior riding experience but Bill was very helpful and ensured that we would still have a safe but fun trip! He was very friendly and was very knowledgeable about the area as well. Beautiful ranch. Thank you for a great day!

My 8 year old daughter, mother in law, and I went last weekend. It was a blast. Bill is so funny and does a wonderful job making you feel comfortable on the horses The horses are soo sweet and you get to ride through some different terrain! Grass, narrow ridges, water, etc.
I would recommend Rocking S Ranch to anyone!

Very pleasant day for horseback riding. Bill was such a fun guide. Horses were adorable. Thank you!!

My wife and I went today. Perfect day, horses were amazing. Bill was a great guide and fun to talk too. Anyone looking for a fun experience, should go here. Very good price for the experience. Will come back in the future.

The owner is so nice and communicates well. He answered any and all the questions we had. The trail was long and beautiful. We will definitely be going again!

This was my first time ever horse back riding and at no time during the hour and a half tour was I disappointed. The tour was a super great time. Thanks Bill you’re 100% a great guy! P.s. if you’re not interested in crossing streams, climbing up hill, or viewing the scenery, go for the great dad jokes!

Great ride with my sister guided by Bill the owner. He entertained us with stories of the area and kept us laughing with his unlimited supply of jokes all while insuring our safety and taking pictures for us!

You will not want to miss this authentic cowboy ride! the best of the West in the East!

My extended family comes into the area once a year and we always make sure to do a trail ride here. This will be our third time here. Bill is welcoming and easy to talk to and always makes sure our ride is fun. One year we had the misfortune of timing our trip with his vacation so we went somewhere else. That made us realize how good we have it here. The trip isn't a boring flat ride. You are going up hills, down, through streams and different terrains. So much fun. Would highly recommend Rocking S Ranch for anyone, regardless of riding ability. He picks the right horse for each rider. My teenage son looks forward to this every time we come. Can't wait for next year!

What a pleasant experience!
The horses are healthy & easy to handle. Bill gave clear instruction to all of us. Safety is a high priority..
Excellent family outing.

Bill is an excellent host who is committed to ensuring his guests have a wonderful experience. He was extremely hospitable and was very willing to work with us beginners. The ride was scenic and had plenty of sights along the way. We will definitely be returning upon our next trip to Winchester!

Bill was our guide and the ride was beyond what we expected! We had a personal experience, tons of fun, and great views. Great time!

My boyfriend and I visited Rocking S Ranch for an afternoon trail ride with Bill as our guide. We had the absolute best time. Bill is warm, funny, and passionate about what he does. We felt right as home from the moment we arrived. From making us laugh the entirety of the trail ride to taking countless photos to document the day, it was such a wonderful experience and I can't wait to get back in the saddle. On a safety note, Bill takes numerous precautions to ensure that his guests are safe and comfortable. His horses are such gentle animals. Thank you so much, Bill!

Enjoyed a wonderfully scenic trail ride through the Virginia hills with Cowboy Bill. As a beginner rider I felt no fear while mounted upon the sturdy and well footed Brooks (as pictured). Bill is an expert horseman as well as a professional photographer. We left with eyes swelling from the wondrous views, minds overflowing with equestrian knowledge/ hilarious jokes, and camera rolls exploding with breathtaking photos! Bill’s genuine kindness and hospitality will not soon be forgotten.

We had a relaxing educational ride with Mr. Bill. He took lots of quality pictures for us on our phone. I highly recommend to support this small business owner! ❤️ The horses are beautiful and gentle.

I had family in for a visit and I'm so glad we found Bill. He took wonderful care of us newbies and had plenty of great corny jokes. Covered a variety of terrain and a couple of stream crossings were a real treat. My granddaughter can't wait to go back. Highly recommended.
Had to add that he took all of our pictures for us with our phone and got some beautiful shots!!

Bill is a really great guy. Nice and funny most important he knows how to take a picture. We did hour and half Riding trail, have so much fun. Rocking Big foot ranch , worth the number one things to do!

It was a beautiful day for a ride! Bill was flexible, considerate, and made sure we left with lots of pictures. He gave us lots of feedback to make sure we were working well with the horses and entertained us with jokes and information about the area along the way!

Had an amazing ride with Mr. Bill, he is extremely friendly and a great guide. The trail was beautiful and the horses were very calm and enjoyable to ride. Highly recommend for anyone looking for a fun getaway, day activity, etc.

Had the BEST time!! Great trail ride, sweet horses, (and great jokes😉) from the best rancher and guide !! So much fun!! Made us beginners feel like complete naturals! A “must do” part of our getaway! Really enjoyed it - can’t recommend this amazing place enough!!

We had a great ride with a great guide! Bill was easy to talk to and gave good clear instructions on how to ride the horse! I’ve never ridden a horse until this trip so it really can be for beginners! In addition to a wonderful ride, Bill offered great ideas of things to do in the area and great local restaurants to dine at! The horses were very easy to ride.

Bill made us feel comfortable from the beginning. He is very informative, took numerous great pictures of our ride with my husband's cell phone, and kept us laughing with his jokes. The ride itself included downhill, uphill, a couple of creek crossings through an area that was peaceful and beautiful. His horses are well trained and enjoyable. The cost of the ride was very reasonable and worth every penny, Bill goes over and above as a trail riding host. Thanks Bill for an awesome ride. Yeehaw!
Jimmy & Kathy Lumpkin

The owner was very friendly and took the time to make sure we were safe. It was a nice and casual ride through the mountains.
We will definitely be returning this fall.

My husband and I took our first horse riding tour and Bill was awesome!!! So generous, easy to talk to and FULL of the best jokes!!! If you are coming to VA and looking for a fun, relaxing experience Rocking S Ranch is the place to go!!! Thank you Bill for an amazing experience and great time!!! We will definitely be back to visit!!!!

Had a good time with my wife. The trail was amazing. The guide was awesome and the horses were great.

The only thing that wasn't great was the porta-john. And the mud path to get to it.

Definitely a five star experience

Me and my two daughters went riding with Bill this past weekend and it was a complete blast! I actually came to this ranch 7 years ago and with that great memory returned with my two daughters. Bill and his daughter are very safety driven and make sure all precautions are taken before as well as during the ride. My daughters loved it all! up and down hills, crossing a small river!!
Beautiful, loved and cared for horses - you can tell they're all loving their place. Would recommend any time!

Visited the ranch for a private trail ride with my girlfriend during a weekend getaway. We met up with Bill who from the start was charming and loved to joke around and was more than willing to help suggest some great local places. We hopped on Apache and Brooks, two great looking horses that were very well mannered. Bill made it so easy and enjoyable that I felt like I've been riding for years even though it was my first time. The ride was a nice mix of terrain, not some boring walk on a flat road, even my girlfriend loved it and she has ridden horses for years. I couldn't have planned a better time and will definitely visit again if I'm in the area.

Great experience! Definitely a must and the trail was beautiful. I think I enjoyed Bill’s jokes the most haha. Thank you Rocking S Ranch!

Highly recommend Bill and Rocking S Ranch! Being able to ride in smaller groups here is such a plus! I actually feel like I was able to connect with the animals and guide more and overall had a more enjoyable time then my previous experiences. The trails Bill guides you through are absolutely breathtaking!! We went during peek fall season and it was some of the most beautiful nature scenes I have experienced!!

Bill comes with a lot of experience and you can tell his passion for the business radiates through him! He is a hard working man doing something that he loves which only adds to the wonderful experience of Rocking S Ranch. The best part is his hand full of jokes and stories he will share with riders throughout the trail! This really gives the experience that much more character and charm!

Overall, I highly recommend checking this place out if you are looking for a peaceful, relaxing experience through breathtaking scenes!

Had an absolute wonderful trail ride. The scenery was beautiful and open. Bill was friendly, informative, had a ton of jokes on hand, and makes sure you’re feeling comfortable during the ride, he’s also of man of many talents and being a photographer is one of them. 10 out 10 definitely recommend!

We had a great time on our trail ride with Rocking S Ranch. Bill, the owner, was a great guide and very entertaining. The ride goes through the woods, across a small stream and along a mountain ridge. Very peaceful setting.
The ranch caters to small groups, making your ride a very personalized experience.

Let's just get this out of the way, this was the best trail ride I've ever been on. Bill was the consummate professional. He was courteous, funny and just an all-around great guy. The trail ride was scheduled for an hour and a half. We were out for over two hours for sure. The ride was over some beautiful country. Hills, streams and not just flat lands. Great horses that were well behaved.
I would recommend Rocking S to anyone!

My daughters and I enjoyed a 90-minute trail ride with Bill last week. It was the perfect break from quarantine life! The scenic countryside of northern Virginia, Bill's gorgeous well-trained horses and his cowboy hospitality were therapeutic relief :)

If you are looking for something fun to do in the Winchester area, this is the place to go. My boyfriend, best friend, and I got the pleasure of riding horses with Bill from The Rocking S Ranch this past week. I highly suggest riding for the hour and a half, there is so much to see! He is a very knowledgeable man with so many intriguing stories to tell you while on your horse checking out the amazing scenery. This was my 3rd time riding with Bill and I will without a doubt return again soon. Definitely worth checking out, you won’t be disappointed!

Had an awesome time!
first time riding a horse is no problem Bill, the the tour guide will make you feel at home and make sure you have a great time. Highly recommended and worth every penny!

Bill was the real deal! I hadn’t been on a horse since I was a child but I have always had a love for horses. Bill made my trip! He was funny and put me a ease the whole ride. Such beautiful country and ride. If your worried you can’t handle a horse because of experience believe me if this Californian could do it anyone can. You definitely get your money worth. Bill loves to ride so be prepared that you may ride over the 1 1/2 time but just make sure you schedule a couple hrs and enjoy!

A cool, brisk but beautiful afternoon ride with Bill was just amazing! He was knowledgeable and friendly! You can tell he loves his horses and what he does! Highly recommend Rocking S Ranch!!!

First, I have to start with Bill. He is the owner and was our guide for our trail ride. Bill is a salt of the earth kind of guy you just want to be friends with. He was very professional, extremely entertaining and knowledgeable. Our ride went through a lot of different terrain and he was incredibly instrumental in making us feel comfortable and maintjnf a very smooth ride. Second, the horses were healthy, easy riders and trained very well. Third, if you’re thinking about horseback riding and it’s not at The Rocking S Ranch, change your plans and book there. You won’t regret it!! We’ll be back soon.

Bill was great! Kept everyone entertained the whole ride. Made recommendation for Spring House Tavern in Woodstock & so fr we are enjoying there now too.

We had a great ride with Bill! Knows how to have fun, entertain, and keep us safe. Lots of fun and would definitely do again. Took lots of pictures for us too. Brooks and Leroy (the horses) were nice too!

The best trail guide EVER! The horses are gentle and very easy to ride. You won't be disappointed. I highly recommend a visit to Rocking S Ranch!

I brought my three children to Rocking S Ranch yesterday. We had an amazing experience. The horses were extremely gentle with my first time riders. The trail was beautiful and fun to ride. Without a doubt I recommend booking horseback riding with Cow boy Bill!

Had a great ride even with freezing weather, photos included & plenty of stories and excitement :)

Truly a family-man who loves his horses and land

I totally enjoyed my ride with Bill and 3 other riders. Brook, my horse partner, did his job well!! The trails, up and down the gulleys were FUN. We crossed streams and it even came with snow flurries. I highly recommend*****. Bill, your dad jokes were....funny :):)

Absolutely the best Easter Sunday our family has had in a very long time. Very kid friendly, Bill is a cowboy with a kind heart. Thank you very much for being so thoughtful of our children.

I just loved Bill! He made our experience awesome and memorable! There were six of us riding and Bill. I especially loved that he did not micromanage my young son (age 6) and daughter (age 8). Nobody had to guide my kids holding a rope or anything. His horses were well-trained, and he gave good, clear instruction and guidance. Bill has a sweet personality and kept us laughing on our beautiful and adventurous ride. The ride was long and worth every penny! Don't forget to tip him! ; ) He is excellent! Oh, and he took so many pictures of us all with my sister's phone. I thought that was so awesome and thoughtful! My sister already uploaded some of our pics on here by the way.

Enjoyed the 90 minute trail ride - very minimal roadway use is required to get to maximal nature, which was a real bonus. Leisurely paced, the ride felt much longer than 90 minutes. The whole family (broad age rages) thoroughly enjoyed themselves. The trail runs over good elevation, through beautiful woods and fields, with great views at the top and creek passes at the bottom. The horses were easy for novice riders. Bill is the real deal - always quick with a joke, regularly checking on everyone to ensure a great time and lots of corny jokes. You'v been warned lol. I knew when I spoke to Bill the first time I had chosen well - Bill is communicative, easy-going and committed to your satisfaction. More importantly, he sure seems to enjoy what he does, and that is infectious for everyone riding.

My 12-year old and I went on a trail ride here today. It was my first ride ever and It was fabulous - we went through the creek, up and down hills, and through some muddy terrains. The service and the scenery were top notch. There were some jokes told and a good bit of coaching us and the horses along the way. We will definitely go back! Thanks for a great time, Bill!

Wow! What a fun time. Our trail ride was one hour of smiling, laughing, and enjoying the beautiful scenery. Our guide Bill and his daughter Hayley really made the experience memorable. Hayley was great with our group of kids ranging in age from 7 to 15. She put them all at ease and got them excited about saddling up. Bill took our five kids and two adults (8 horses including his!) out on the trail. We loved his sense of humor—he kept us laughing the whole time. Both Bill and Hayley prioritized safety and we felt comfortable the entire time, even those of us who had never ridden a horse before. Bill was great with instructing the kids on how to steer and manage the horses. The kids all got helmets to wear. Bill took a ton of pictures for us while we were riding so I could have pictures of the whole group (he doubles as a great photographer!) My favorite part was getting to go through a stream several feet deep. For once, our entire bunch of kids had a blast (usually with the range of ages someone isn’t having as much fun, but not in this case!). I highly recommend the Rocking S Ranch for horseback riding. It was well worth the money, and as a bonus they are less expensive than their competitors. One word of caution, the driveway into the Ranch has been washed out a few times, so use caution going on it or just park on the street. Thanks again Rocking S Ranch!

If you'll believe it, this is the first time I've ever given a 5-star rating and that's because Rocking S deserves nothing less than "excellent" feedback from me. In fact, five star bursts best describes our experience. Pow! Pow! Pow! Pow! Pow! That's five bursts. Count 'em.

Visiting Winchester, VA, from the Boston area, for my kid's Feb. school break, I wanted to line up some activities she would be thrilled to report back to the classroom upon returning to school. Winchester, VA, has a lot to offer with it's rich American history, pastoral setting/scapes, natural wonders, cool places to eat/drink and...HORSES. So very many options, but my kid is 7yrs-old and, for a 7yr-old, horses are magical. I wanted to make magic, but that's a tall order. How was I going to pull this off in a matter of 5 days? A: Rocking S Ranch and a guy named Bill.

In 90 minutes, Bill delivered magic, adventure, challenge, an education and laughs. How did he pull that off? Is he a wizard? He was a pleasure to speak to over the phone and, in person, he earned our trust within minutes. As a single mother, trying to give her kid the world, trust is a huge thing. Trust is a make-or-break deal, you know? Bill put our safety, and the safety of the horses, first and was stern with commands/instruction, in the way necessary, to guarantee a comfortable experience for all. I appreciate, very much, all the time/energy/resources he puts into the ranch, all on his own, to share his world to others. The trail gave us some beautiful views and all the challenges/fun we could have hoped for - a good fit for any level of experience. The ranch itself is a no fluff, working ranch but peppered here-and-there with kitsch that appeals to out-of-towners/other-worlders while somehow managing to seem authentic and true to the land, animals and that guy named Bill. Again, is it wizardry?

Our trail ride at Rocking S was our first, ever, and the bar is set HIGH. Thank you, Bill, Apache and Brooks for the magic. You'll be the talk of the classroom, next week, and this isn't the last you've seen/heard from us!

P.S. The dad jokes. So many dad jokes. Oh, boy. The jokes.

Cowboy Bill is the real deal! A great time had by all. Kind horses, a beautiful view while Bill will tell a joke or 2. My girls had zero riding skills they felt comfortable and safe.

My partner took me out to Rocking S Ranch for my birthday. First time horseback riding. Bill was super friendly and personable right out the gate. Both him and I are locals so we had plenty talk about. The trail riding was superb. A great deal of diversity in terrain and scenic views. Furthermore, being that I was a beginner, Bill was direct and informative about riding instructions. We knew We were in good hands the whole time. Will definitely be returning in the fall.✌🏼

Great time, the area is gorgeous, and worth bringing friends and family of all ages. He is a hoot and a half, and will keep you entertained the whole ride

The owner was very accompanying and the horses were great. Highly recommend this place if you’re in the area!

Excellent trail ride through the woods and across a creek.

Trail guide Bill is informative and funny.

Horses are well kept and sure footed.

What a fantastic experience! I've been on trail rides before, but on those, the horses just plodded along a well-worn, flat trail. With Rocking S Ranch, you're expected to steer and direct your horse, and the trail goes through woods, across streams, up and down ridges, etc. It was beautiful and exciting! I took my daughters, 8 and 10, and they had such an amazing experience. They were a bit nervous at first, but Bill game them clear instructions and guided them through the ride. Bill was so helpful and also told jokes along the way to keep everyone at ease. If you're anywhere near this area, I HIGHLY recommend going.

Bill was friendly and awesome, he cracked jokes while we were riding. This was our first time horse back riding. He made sure that we were safe and comfortable throughout the ride. He did not rush through the trial, also one important thing he took a ton of pictures on our mobile phone during the ride free of charge :)

Booked a ride at Rocking S Ranch for my wife’s birthday, and Bill made it a memorable experience! The area was beautiful, the ride was diverse and Bill captured some amazing pictures that we’ll appreciate for many years. In addition to being a great guide and funny person, he had great recommendations for local food and lodging. Will be back for sure!

Such a great experience!!! Me, my mother and sisters had such a great time! I highly recommend the Rocking S Ranch to anyone!

I had the most amazing time today riding with Bill! I went by myself and had so much fun. I felt super comfortable with the horse and during the trail ride. Bill is very knowledgeable and clearly loves his horses and wants to give you the best experience. Any couple, besties, or someone who wants to ride a horse just because! Bill is your guy. I will definitely be coming back!! Thank you so much! Happy trails!

We decided to stop here as a fun way to stretch our legs on our vacation. It was off season, but they accommodated us anyways and were SO kind! The customer service was unlike any other! We will definitely be back sometime, it's such a fun experience!! We recommend this for everyone!

Bill was such an amazing guide. Extremely helpful with information about the town of Winchester. He was very nice and was rolling with the dad jokes the entire trail ride. He was clear with instructions on how to handle the horses but not strict or tough where it was made uncomfortable. He was patient and welcoming. High recommend!! The area and trail are all absolutely gorgeous. Will definitely be back

This is a really wonderful trail for a horseback riding. Not too challenging, and not at all flat and monotonous. It’s a very scenic area with beautiful woodlands. We crossing through a creek, and travelled up and down mountain trails. Horses sweet and gentle. Perfect for us as older, inexperienced riders.

My daughter and I found Bill and his Ranch to be informal, inviting and entertaining. Bill provided us a relaxing trail ride on Brooks and Leroy! He tells lots of jokes and by the time you are done with the ride, he feels like he’s family!

Great place to go horseback riding. Highly recommended for anyone wanting a great experience. Great instructor and wonderful scenery.

Lovely scenery with a very friendly guide. Bill did a wonderful job creating an entertaining experience!

We had such a good time. The horses were well mannered and Bill (the owner) did a wonderful job talking us through how to safely tell the horse what to do. We don’t have experience riding and I was a little nervous to take my eleven year old cousin but we had no issues. I highly recommended this place.

Had a great time with my two kids(10 & 9) on a trail ride through the woods and across some water! First time for my kids on horses and they both are ready to go back and do it again. AND SO AM I!

Rocking S Ranch is a great place to visit! I’ve never rode a horse before, so Bill did a great job showing me the ropes!

Thank you Bill & Haley! We had an absolutely amazing time! My boyfriend and I booked this excursion through a local bed & breakfast (L'Auberge Provençale), and we loved every minute of our ride! Bill took amazing photos for us, and kept us informed and entertained the entire time. It has been years since we rode horses, and he gave us great pointers and a wonderful ride. Definitely a must-do if you are in or around Winchester!

Me being a beginner at horse riding had some reservations if this is going to be a good experience for me, but I enjoyed this ride to the fullest. Amazing forest area we had a creek crossing uphills downhills just perfect. Our horses were amazing and Bill is a great guide! Loved the jokes, enjoyed the ride we’ll be coming back for more.

We were looking to do something adventurous for our 25th Wedding Anniversary on our trip to VA and this hit the spot! Bill was great and made the trail ride memorable. Bill was familiar with where we were from in NJ so that made good conversation, too! Bill took lots of pictures with the cell phone on our ride, capturing the moments for us. After the ride, I was lucky to receive the special Rocking S Ranch "branding" on my car, which you can only get if you really go for the trail ride! We checked out the sites in "Old Town" Winchester that Bill recommended, had an amazing anniversary dinner, and everything was great! When we make it back to Winchester someday, we plan to visit Rocking S Ranch and Bill again!

Took an enjoyable ride with Bill. He took us through some beautiful country with interesting commentary. His horses were gentle and easy to guide. I read others say he was difficult to reach and in fact we each left voicemail for each other but, nothing out of the ordinary. It’s a small family business a cowboy hat is just one of the many he wears. If you’re in the area and looking for a trail ride give him a call, you won’t be disappointed. ⭐️⭐️⭐️⭐️⭐️

We enjoyed the colorful conversation and corny jokes along with some fine trail horses and green trails!

What an excellent experience! There is a reason Bill is so well-reviewed and greatly appreciated in the area—he really knows how to have fun! My wife and I took a trail ride with Bill through the beautiful surroundings during our honeymoon road trip. It was easily the highlight of our time in Winchester. Bill is very knowledgeable and really is a great guy. And his sense of humor was an added bonus—many new "dad jokes" were learned for the repertoire! If you are in the area, I cannot recommend Rocking S Ranch more! You won't regret it!

My wife and I came to Winchester for our anniversary and we really enjoyed riding the horses. We got to meet Moose the cat and we spent 90 minutes riding on the trail. We enjoyed the time we spent here and would definitely come back.

What a great fun filled time we had at the ranch
Wild Bill is the BEST guide with lots of jokes along the way ! Breath taken views absolutely beautiful !
It is definitely a must when visiting Winchester
My husband and I are planning another ride for next month!

My family had a great time with Bill at Rocking S Ranch, the horses were perfect, the scenery was stunning and Bill as a guide was superb. Would definitely recommend and would love to go back some day!

If you are looking for the quintessential horseback riding experience, look no further. THIS IS IT!
An awesome ride with our guide, Bill, a true American Legend!
The scenery was beautiful, the weather perfect and Bill did an outstanding job of sharing his knowledge of the area and his experience as a horseman.
Don’t pass up the chance to lose the world and perhaps find the you that you’ve been searching for out on the trail.
Hope to see you again soon, Bill!

Steve & Dannie

My cousin Molly and had the most amazing time! Bill was so kind and very welcoming. He is someone you’d like to sit down and talk to over a few beers! He makes you feel right at home and safe riding his horses. I will be going often and I can’t wait to bring my kids out.

We had a great time with Bill, the horse were great, and the ride even better. This is no lap around a pasture, this is a great trail ride threw the great outdoor. From beaver cut trees, crossing streams, searching for bigfoot lol (sorry darryl), and red fox sightings (sorry lamont). This is a trip we will definitely make again thanks Bill.

The 1.5h trail rides with Bill, the owner of Rocking S Ranch, have been an outstanding experience for my two kids and myself. We loved it so much that we went for a second time three days later. The second time Bill took us on an even more exciting trail. My kids of 8 and 10 were entirely inexperienced with riding but perfectly safe and happy on their horses at any point in time. Bill's horses are very well trained, patient, calm but alert and agile. Needless to say that the northern Shenandoah area is certainly one of the most beautiful in the United States. The kids also enjoyed playing with the Ranch's cats. Riding out with Bill is a must-do in the area!

Bill was great with our large group. Tucked away in Winchester, Virginia, this ranch tops my list of fun things to do outdoors.

Bill is such a down to earth country guy, he really made our trail ride such an authentic experience for me and my fiancé! So happy we chose his ranch for our first real experience horse back riding. His ranch is his home and he made us feel like we were visiting family. We felt so welcome with Bill, he had us laughing the whole time.

Bill and Hayley were absolutely fantastic. They made us very comfortable and my kids very well enjoyed every minute of it. The horses were so well trained and calm that it made the entire process so enjoyable. Will definitely tell all my friends and will definitely come back again!

Great time. We would recommend it to everyone. The trail was perfect. The horses were awesome, and the owner/guide made the trip.

We had a BLAST here while on our honeymoon!! Bill is a great guy and our horses were lovely & gentle

We had an absolutely amazing time during our trail ride. Bill was a great tour guide and mixed it up with some dad jokes!! We went through water several times and we went up and down hills. It was a fun challenge and the horses were nice and cooperated well (except they liked to eat, but who wouldn't?)

We had a wonderful time with Bill and his horses! He took the time to get to know us and he was hilarious the whole ride. The trail itself was lovely and the horses were well taken care of and gentle enough to suit an amateur rider. We highly recommend the Rocking S Ranch!

Bill at rocking s ranch created such a great experience! He truly knew how to entertain and made our trail ride a time we won't ever forget. If you're looking for horseback riding this is the ranch to go to!

We had an AMAZING time with Bill. The ride was amazing, and he took TONS of pictures for us. If you ask nicely, he will throw in some free jokes too! 10/10 will come again.

The scenery is beautiful. The horses are nice, well behaved and healthy. No phone, no traffic and so calm. It was the perfect mother daughter time. We will certainly do it again! Thank you Bill for the wonderful ride and the funny jokes!

Bill was very accommodating, he was able to get us right in for our trip. This was my husbands first time actully riding. Absolutely loved the horses!! My husband and I had a great time. Bill was a great guide and funny. Beautiful scenery. Well worth it!!! You will not be disappointed.

My daughters and I enjoyed a fun family excursion with Bill as our guide. He provides entertainment on the ride and even documents it all with your own cell phone! Definitely worth a drive to Winchester. Come out to support this family business.

The best trail ride I have ever been on. Amazing views. Being able to ride through different terrains - grass, water, concrete, snow. Meant for a beautiful ride with some great pictures. Definitely check this place out, some very romantic spots and great for anyone who is a beginniner with horses. Definitely going back and cannot wait for it!
Bill has great craic plenty of jokes to make the ride stand out from others. Him and his daughter are awesome and put so much work into it, it is just amazing!!

Truly, an amazing, down to earth, simple way to get away from your everyday stressors. My partner and I live right outside of DC and needed to get away. This was one of the first things that popped up on our 'to do list', and we are SO happy it did. We had such an amazing time not only riding with the horses, but the owner (Bill) himself was beyond kind, loved telling stories of his children, full of jokes... It was honestly everything we really needed at the time. Bill made it VERY clear that we were going to get some amazing photos, and boy did we. I cannot thank him enough for taking us on such an adventure that we didn't even know we needed. Worth EVERY penny.

This was such a beautiful, fun, family day. Bill is a terrific guide. I am 54 years old and had never ridden a horse and neither had my 58 year old husband and 18 year old daughter. It's something that I have always wanted to do. I have very high anxiety and get very nervous about things, especially new things. I also don't usually leave reviews but I rely on other's reviews in determining what decisions I make about things I want to do. Bill, the owner and leader, made us so comfortable. The horses we had were perfect for us and we did an amazing 90 minute trail ride through the woods and streams of beautiful Winchester, VA. It was truly perfect for a first time rider or any level of experience. We can't wait to hopefully make it back some day. Thank you, Bill, for making our day and weekend so special! I highly recommend!

This is my second time at Rocking S Ranch! Best way to celebrate my birthday. Love it so much. Bill is very funny and nice! Would definitely go back again. Thank you very much Bill for another wonderful experience!

Rocking S Ranch is a must do if you are in the Winchester area. The trails are beautiful, the horses are sweet, and Bill is awesome.

My family (two pre-teen boys, father-in-law, wife, and me) spent a lovely late March afternoon riding the trail with Bill. All of us were riding novices, but Bill got us each set up on an appropriately sized horse and taught us the basics. My boys thought Bill was hilarious (and I added some good Dad jokes to my repertoire) but even more importantly, Bill did a great job of coaching the boys past their nervousness about being on top of, and in charge of, an animal ten times their size. Bill's extensive experience with his horses (and with new riders) shone through -- authoritative but never pushy, engaging but not garrulous. And the trail went through some really pretty terrain, including fording a small river. A highlight of our spring break vacation!

Bill was awesome with my 10 year old daughter, whose first time on a horse was more daunting than expected. Fun time!

My family (with children ages 7-13) visited picturesque Winchester, VA specifically for a trail ride with Bill at the Rocking S Ranch. It was well worth the drive and provided the escape from the city that we were hoping for.

Bill gave our family the time and attention that made our trip so enjoyable. He taught us the skills we needed, then treated us to a fun, yet challenging trail ride.

We are definitely beginners, but the horses yielded the perfect amount of control to us.
We felt capable and comfortable even in some areas with difficult terrain, including climbing and descending hills and stream crossings.

What a great experience for our family! Thank you, Bill.

This was truly an awesome experience!!
The horses are beautiful, the guide was amazing and full of knowledge and experience.
The scenery and the trail is wonderful!!

All around wonderful experience! The only thing better than the colorful scenery, was the warm and generous hospitality of Cowboy Bill. Truly one of a kind! Bill took his time educating us (whether you're beginner or experienced) and he disarms you with his easy going nature. Call ahead, call early, leave a voicemail; we were lucky that our persistence paid off because a party ahead of us did not have CASH so they canceled and we were able to ride at our leisure after 3pm. We will most definitely return to Rocking S Ranch in support of our new friend Bill.

What an awesome way to spend the afternoon! Bill the tour guide was awesome and funny!! Bill’s horses are so gentle and well mannered!! Couldn’t have asked for a better horse ride! Beautiful country to take a ride! Bill also takes awesome pictures! Very good place for the beginner rider to the most experienced rider!

an absolute amazing view, amazing horses and just over all a great experience. will definitely be going back!!!

Amazing experience on a beautiful Easter Sunday. It was my first time riding a horse and Mr. Bill made my experience so wonderful. I will be back. From West Coast of Africa to Virginia, 🇺🇸.

We all had the best time today at Rocking S Ranch. Bill did a great job taking us on the trails. His horses are well trained which makes it for a fun and easy experience if you have never ridden before. Bill has a great sense of humor which kept us laughing the entire time. Our family really bonded with Bill and his horses. You can’t go wrong with the Rocking S Ranch

Had a great time with my family. Bill was very friendly and personable. He took a lot of pictures. Terrific experience!

Bill couldn't have been more accommodating. I called day of for my girlfriend and I to go and he fit us into his day. The horses were extremely docile and the trails were scenic. An honest Virginia horseback riding experience. We will be visiting again soon!

My friend Jill and I had a great ride today. The horses were well behaved and Bill was very funny and entertaining. I would highly recommend anyone looking for a trail ride to check out Bill and Rocking S Ranch

Great time, great ride. Scenery is incredible. Bill is a great guy, great guide, and always entertaining! Worth every penny…

Bill (the owner/operator) was fantastic! Our 90 min trail ride was more like two hours. It was just Bill, me, and my mom. The ride takes you through the woods, up and down some inclines, and through a creek (twice!) Horses were very gentle and well-behaved. Bill regaled us with stories/jokes and information about the area. We were staying at the Salamander Resort but booked our horseback riding at Rockin’ S because the price was way better and the ride was longer. Highly recommend!

Bill treated me, my wife, and our 7 y.o. daughter to a great time on two days' notice on a July 4th weekend. Nothing fancy, just plain fun for three beginners on an easy ride through woods and water. Very close drive from Luray Caverns/Shenandoah Natl Park or Harpers Ferry, Bill welcomes day trippers from DC, we'll recommend to friends.

My wife and I had a great time! Bill is very knowledgeable, friendly and a great guy all around. On the ride we crossed two creeks and climbed and descended several hills through varying terrain. The day was perfect...we look forward to visiting again soon!

Since I can remember I've always wanted to ride western, being a avid horse rider in the UK ive only ever known one style of riding. Well today my dreams came true and i honestly couldn't thank Bill enough for making this experience an utter delight.
Wonderful scenery, beautiful horses and what a utter gent Bill was.
I would absalulty recommend this ranch to anyone who wants to experience the stunning virgina woodland. If i could rate Bill and Hayley a 10 out of 10 I so would!
Thanks again

Bill and Haley were amazing! The whole ride was a wonderful and the views were breathtaking. Definitely recommend this to anyone who loves nature.

My sister and I had a fun time. Jim was a great guide and knowledgeable of the land. We had a relaxing time. The horses were easy to ride as well.

I have been on plenty of rides but this one was by far the best one ever. My husband and I rode with another couple who we actually had lunch with after the ride. During our 1.5hr ride( $60pp) we went through waters which was AWESOME, up into the mountains, and even in dirt roads!! I can honestly say I’ve ridden on a bunch of different surfaces😀 Bill, the owner, was our guided and he was very entertaining with his odd jokes. Made the ride more interesting and less intense. All around a great time! I will def be back again! Highly recommend this place!

Rocking S Ranch pops up on google when searching for most scenic horseback riding trails from Winchester, VA. As I continued my search I kept coming back to the page, not only was it affordable, authentic, and charming, but it also has the highest rating with the most reviews. After a promptly returned call, (the ranch is family ran so best not just show up and have to count your losses as he seems rot book quickly) on we went 25 minutes away from old town. Upon meeting Bill he warmly invited us to relax and get acquainted with the friendliest cat, Moose, as he finished up a ride, He was kind, efficient, patient, and as full of dad jokes as he is knowledge of the land around him. It was a pleasure hearing all about his lovely daughters, and vast local know how. He made sure to get to know each of us personally, without intrusion, and took literally two hundred pictures with my phone, allowing me to observe the beauty of the ride undistracted. Thank you sir we will be back and so will our friends! 10/10 recommended, you go anywhere else you're missing out,
~Ashley from VA Beach

We are new to the area and wanted to take in the local fun. We sure found it at the Rocking S Ranch. The ride was gentle, so kids will have a great time too. We walked through stream and forests and Bill, the owner, was very knowledgeable. We had a lot to talk about since he was from New Jersey also. Good experience. Thanks Bill.

This ranch had such a cool vibe and was beautiful. The guide, Bill, is not only the most lovely person, but he also has THE BEST horses. My boyfriend and I are by no means good riders, but it was very easy to ride and a really fun experience.

My wife and I took our seven-year-old granddaughter to the Rocking S Ranch for her first-ever trail ride. Bill was our guide, and he could not have been more warm, patient, helpful and good-humored. All of our granddaughter's anxieties disappeared when she climbed up on her horse. Bill took us through woods and meadows, down hills and through a creek, leading her horse in places but letting her ride independently when appropriate. It was a leisurely 90-minute ride that she will never forget -- and fortunately, Bill took many photos with our camera to document the experience. A perfect morning in every way!

From Honolulu to Winchester ! The kids , age 19 and 17 had a great time . Bill entertained them along a gorgeous trail ride and made it a special time for them.

Bill was AWESOME!! We had a great time on the ranch and will be returning. Would definitely recommend!

Bill & Haley at the Rocking S Ranch were incredible!! Our ride with their calm and easy going horses was a blast. The ranch was easy to find and Bill’s price for an hour ride is very much worth it. Bill is a throwback and made us feel loved immediately. Go see Bill and have some fun! Go Florida State!

I went solo and worked in with a family. Bill called me back same day to work me in. I am so glad because had an amazing time connecting to nature and the gentle and strong horse Rio. Bill was great at taking time to teach us every step of the way of how to ride and handle the horses. Bill also kept us entertained with jokes all along the trail. Yee Haw! What a wonderful time for an individual or for a family. Bill will make you feel like one happy family. I'd like to take my boys next time.

The experience was amazing from the time they helped me mount up till the time the helped me dismount. Thanks to a friend I got to ride for the first time in over 35 years. It was so much more than just a ride over a flat trail. We went through creeks and up and down small hills and heard wonderful stories and really bad jokes but it was the best day that I have had in so very long. Thank you Bill, Hailey and Leroy.. I will be back soon...

Had a fantastic ride. The owner and guide, Bill, was great with everyone, especially our kids (ages 10 and 7). It was their first time riding and he made them feel comfortable with perfect instruction and encouragement. He took his time to ensue everyone’s safety. A great story teller. Perfect family experience and true family run operation.

I recently went on a 1.5 hrs trail ride. Bill is an excellent guide and very communicative. He was completely aware of every rider in our group, making sure everyone was safe and having a good time. We traversed a variety of terrain: steep downhill and climb, river crossings, and a boggy swamp. Fantastic ride, and a great value for the price of $60. Tip him well because he deserves it! Very satisfied.

My friend and I had a great ride through beautiful, varied terrain including water crossings and hills. Bill is a knowledgable and entertaining guide/host that provided a fun and safe experience for horse riding novices.

We stumbled upon the Rocking S Ranch on our last day of vacation in West Virginia (July 7, 2018) and it was the perfect end to our trip! Bill and Haley exuded calm and experience with both the horses and our kids (Ages 8 and 11)! Bill tailored the ride to fit our family and we all loved it. With Bill cracking jokes and anecdotes during parts of the ride, and with all the horses steady and sure, we loved the ride and look forward to returning to the Rocking S Ranch. Just watch out for Bigfoot!

From making the reservation to saying goodbye to Bill, it was all a great experience that we will never forget. My uncle was visiting from overseas and out of all the places and activities i had planned for him, this was by far his favorite. It was our first time riding horses so we were a little intimidated at first, but Bill made us feel so comfortable with his awesome vibes. The horses are so well trained, the scenary is beautiful, and Bill was nice enough to take a billion pictures of our experience that we will never be able to forget. I will definitely be back with more family and my kids.

This was a lovely way to see the beautiful countryside. We are both beginners and felt at ease with Bill as our guide. I would highly recommend a trail ride at Rocking S Ranch

Wanted to do something fun when visiting our son who attends JMU so we booked a trail ride at Rocking S Ranch. This was THE PERFECT DAY TRIP! Only a short ride from campus and you will have a memory that lasts forever. We did the 90 minute trail ride through some of the prettiest country I have seen. The ower Bill made it easy and so enjoyable. He is amazing!!! A great guy who takes great care of his horses. He makes the ride amazing. Tons of great jokes and you leave as friends.
Can't wait to come back and ride again. Truly a must do if in the area.

We had a very scenic ride through meadows and woods. Wonderful view of the mountains and crossed the creek. We even saw a deer!

Bill was very entertaining on the ride and was a great trail guide. He gave instruction and would stop to make sure we were all together.

My daughter and I so enjoyed riding with Bill ! The scenery was beautiful and Bill shared stories and his great sense of humor . Horses were sweet and beautiful . Highly recommend … will be seeing him again when my daughter comes home again !

We had a great time riding with Bill. He keeps the ride entertaining and informative and takes great pictures too. The trail is adventurous but doable even for first time riders. Highly recommend!

We went as a family of 4 and everyone enjoyed the experience. Great scenery and very pleasant guide. Lots of corny jokes that kept everyone smiling.

Had a wonderful time. Brought on a great trail ride with fantastic scenery. Our guide was excellent at trying to engage my son, which isn’t easy, and gave all of us an amazing experience that we will remember. Would definitely recommend.

Yep, horseback riding and being in the out of doors. My family enjoyed themselves thoroughly while we were out. Great weather by pure luck. Our guide, Bill (and owner) kept our daughter on her heels (a rarity) with all his jokes along the way. Most amusing was ol 'Leroy'. That horse has his own agenda and way of going about things, still, a gentle animal and certainly worth a visit. Scenery was great and just enough to give you a feel (or defamiliarize yourself) with trail riding.

My friends and I had a wonderful time here! Bill was very kind, accommodating, funny, and just an all around great guide - and the ride itself was lots of fun. I'd definitely recommend Rocking S Ranch to anyone looking for a great horseback riding experience in the area.

This was my 7 year old's first trail ride. We had a wonderful time. Bill is a great guide and great with kids. He is knowledgeable about the area and the trails. The horses were gentle and the scenery was beautiful.

Would highly recommend. Bill does a great job of tailoring the ride to your skill level. Also keeps it interesting along the way and helps with good pics. Beautiful scenery, nice horses and a friendly guide. 10 out of 10!

Bill was so personable and friendly from start to finish. My family and I went on an early afternoon ride with Bill, and had the best time! He was so great with my sons, ages 6 and 9, and helped them stay confident on their horses. I felt safe and secure the entire time with my family in his hands, which was really important to me. We went through a beautiful trail in the northern Shenandoah Valley, through the creek twice, and even down and back up a steeper trail. We were all beginners, but felt like pros by the end of the ride! The horses were beautiful and Bill matched their personalities to each of us perfectly. It was so fun! We were all sad to leave the ranch, and truly felt like Bill genuinely cared about us. He is such a great and patient guy, and a wonderful teacher and leader! He had funny jokes and good info, and I really appreciated the pictures he took of us and will cherish them! I highly recommend a trail ride with Bill! We all agreed that it was our favorite activity while visiting Shenandoah National Park.

My family of four decided to visit Winchester for Labor day weekend getaway. Rocking S Ranch was the perfect addition to our trip. Bill was accomadating, kind, patient and informative. The trail horseback ride is for anyone, experienced or inexperienced. I definitely recommend! Have fun!

It was my first time riding a horse, and to be honest, I wasn't expecting that much. However, after spending some time with Mr.Bill, I was so relieved that I decided to go on horse riding. Even a beginner like me really enjoyed it, and you get to see the beautiful view around the hills. Quality time spent, definitely worth going.

Great time! Highly recommend coming here. Bill was fantastic and very welcoming. Many laughs and beautiful sceneries to cherish. Bill was thoughtful, at the beginning of the trip he took one of our cell phones to take pictures throughout the whole ride for us to always have and look back on :). I will certainly be coming back!!!! Such a wonderful experience.

First time riding a horse, and it was a great time! Bill was an awesome teacher, very patient and skilled, and his jokes were the best! We went for our anniversary and had a wonderful time. The trail was very versatile and exciting.

You cannot ask for a better time or a better guide than Bill. He makes the day so enjoyable and the horses were wonderful. I will definitely return for another adventure.

The entire trip was a fantastic experience. Our guide, Bill was very knowledgeable and entertaining. The horses were very well cared for, disciplined, and we were extremely comfortable on the trail ride. If you are searching for a trail ride experience and are a novice at it, Bill is very patient with his instructions and will guide you all the way.

More than your average pony trek. Bill mixed up the terrain to keep it interesting. Learn about the horses and their personalities. Temperatures permitted an afternoon of riding in January. Great to get outside in the fresh air. If you’re in the local area and want to ride call ahead and book! Fun time that will stay with me for a while.

Thanks to Bill and Rocking S Ranch for a wonderful experience. Our family had very little riding experience. We were welcomed at the Ranch and Bill and his family ensured we were all comfortable on our horses and able to enjoy the beautiful scenery and landscapes in the Winchester area. He immediately sets you at ease and teaches you all the basics to enjoy a wonderful day outdoors with nature. Couldn't ask for better horses. We had a great day! Hope to be back soon and will sure recommend this experience to our friends, neighbors, etc. Well worth the trip!

I took my son and his 2 friends on a 1.5 hour trail ride. Bill was an outstanding, patient, and quick witted guide. He was patient with the kids who were all new riders and had plenty of witty jokes. The trail through the woods and over the creeks was absolutely beautiful. The horses were very calm and easy going, which made my first time cowboys much more comfortable. I would definitely suggest this sweet, little ranch for anyone looking to get away from the hustle and bustle of modern day life!

This was a wonderful experience. Bill is friendly and puts the horses and their riders at ease. The scenery was beautiful. The horses were well cared for and responsive to direction. I would do this ride again and again and recommend it to ANYONE.

If you want to enjoy a trail ride, this is the place to go! Bill and Hailey are great people and you will not be disappointed. Family owned so they really do care if you have a good time! Cant beat trail riding with a real cowboy. Cant beat the scenery and Bill is also your photographer and joke teller. We will definitely be back! Thanks again Bill and Hailey we had a blast!

Our family visited the Rocking S Ranch this past weekend and went on a trail tour with Bill. The whole experience was exceptional. Our 9 year old said it was the best day of her life. Bill expertly guided all 3 of us, making us feel comfortable riding horses. Beautiful scenery, friendly horses, and a knowledgeable and humorous guide. What more can you ask?

We could not have been happier with our recent experience at the Rocking Ranch. Nice to go to a place that is all about their clients and clearly not in it just for the $$. Truly the definition of a family business. Beautiful trail that went through streams and scenic hills. I can’t wait to take our boys to this place too! I highly recommend Bill’s Rocking Ranch!!!

Bill went above and beyond to make sure that we had a memorable experience for the day.The horses were clearly very well taken care of trained trail horses. This is for sure a place we will return & that I feel comfortable bringing my two rambunctious 6&8 y/o sons.

Thank you Bill for an amazing afternoon trail ride!!!! We had so much fun today! Enjoyed the beautiful woods, blooming wildflowers and great laughs! Can’t wait to come ride again soon!!!
Would definitely recommend the ‘Rocking S Ranch’ to anyone looking for a spectacular trail riding experience.

I had a fantastic time! Bill was very funny the ride just flew, wish I could've stayed even longer!!

Bill is the real deal. Trail ride through the woods, up and down the mountain, through meadows and streams. Horses are sturdy and tough. Fun. Beautiful. Will be back!

A group of longtime friends, we were looking for a fun new activity. When one of us suggested trail riding, we all were excited and Bill did not disappoint. We had a great time riding over varied terrain. Bill is an expert guide and we had a blast!

My husband and I had one of the best days ever at the Rockin S Ranch with Bill and Hailey! We were heading to Winchester to visit my in-laws and were expecting a nice warm day in January and wanted to enjoy the weather...we found Rocking S Ranch on Trip Advisor and saw that it was open all year! We were able to schedule a ride with Bill and after dropping off our kids for a grandparent's weekend we wanted to do something fun just the two of us... and yee-haw, was this it! The scenery was gorgeous, the horses were adorable and the company was engaging. I think we were doing pretty well riding because we were able to gallup through the woods off the beaten path, go through a creek and generally just feel like cowboys! I used to do these kinds of mountain trail rides when I was little and have been looking for something like this for my kids. I will definitely be taking my two little ones when they are a little bit older but will also be going again with just my husband because this was a perfect date!

Great experience new riders quickly become old pros when you’re learning from someone who truly knows and loves horses. Great way to experience something new and learn from an experienced veteran couldn’t have been a better day great for any age

My sister and I went today and had an excellent experience! This was the first time my sister had ever ridden a horse before and Bill was a great instructor and made her feel so comfortable and safe. Gorgeous views even for an overcast day. I definitely recommend this trail ride for everybody.

Plus they have some beautiful horses :)

What an amazing time for the whole family! Beautiful views and trails, wonderful gentle horses, and Bill made sure to cater to all ages. It was such a fantastic experience and great instruction - if you’re looking for an easy and relaxing way to introduce your kids to riding, take advantage of this guided trail ride and go right along with them. We had smiles all around and both kids are eager to ride again and again.

My fiancée and I spent the afternoon at the Rocking S Ranch. Bill, our tour guide, was amazing, funny, and put us on the trail for adventure. I would highly recommend the Rocking S Ranch for anyone regardless of riding experience as long as they are looking for a great event!!!!

My daughter who is 12 and has never ridden a horse and myself came to Winchester just to ride with Bill. He came highly recommended by a family member. He absolutely did not disappoint. He put us at ease right away and he is a very nice and personable guy. We enjoyed the ride from beginning to end. If you want a real trail ride this is your man. He’s very experienced and despite that his rates are very reasonable. He also tells the best jokes. We will definitely be back to visit. Thanks Bill!

My husband and I were visiting Luray, Virginia for the weekend, and we booked a 1.5 hour trail ride with Bill. What an enjoyable experience! It was worth the hours drive from Luray. I had not ridden since I was a teenager, but Bill made me feel comfortable and made sure we were all aware of what we needed to do before we started the ride. The trail was wonderful, and the horses were great. Bill was also very knowledgeable and funny with his jokes throughout the ride. We would definitely do it again with our family the next time. Thanks Bill. We are so glad we met you and would recommend others to come visit and ride.

We were looking for outdoor adventures during these strange times of covid. We left the city and had a wonderful trail ride with Bill at Rocking S Ranch.

It’s not your typical trail ride around a groomed pasture, we went through some beautiful woods and crossed a creek a couple of times. We rode two very sweet horses Brooks and Apache.

After a fun trail ride, Bill suggested we enjoy old town Winchester and gave us some suggestions for a mid-day meal.
We had a beautiful day and highly recommend Rocking S Ranch and Bill if you are looking for an adventure too.

We were on an escape into nature and looking for an opportunity to go for a trail ride. Bill gave us a great orientation and provided an entertaining adventure that never felt rushed, timed, or shepherded. We felt safe and entertained and enjoyed getting some fresh air with great company and experienced animals.

Bill is all about customer service... I had a fantastic ride just the two of us, with great conversation (and lots of dad jokes), diverse terrain, and his photography skills will surprise you. Definitely a must do if you’re anywhere near the Winchester area.

I’ll definitely go back.

Absolutely loved it! The trail was beautiful and Bill was very nice! The horses were very well trained and so pretty! Would definitely recommend!

Just had a wonderful 90 minute trail ride through some gorgeous countryside and woods with my three teenage daughters. Peaceful and serene, the trip was a great bonding experience. Being beginners, Bill made sure we were safe, and was very accommodating, letting us add an extra rider on short notice. Thank you Bill!

This is by far the best trail riding place I have been to yet! They make you feel right at home and welcome you with open arms. Very safe and adventurous trails that help you appreciate the amazing nature around you! Looking forward to a return visit!

Ride was a great experience for our family group, Bill was very safety conscious and had us laughing with his jokes .The horses were very calm and gentile . I would highly recommend the Rocking S Ranch for your next trail ride

My fiancé, daughter, and myself have been meaning to schedule a time to go on a trail ride for awhile and oddly enough the best day that worked out for us was on Easter day. Bill was not only available but willing to make time for us at the ranch on Easter! The weather turned out to be warmer than expected and thus made it a lovely day to take a trail ride that takes you along the road, through the mountains and creek. What made this such a wonderful experience was how personable Bill was and how intimate it was being out in nature, stopping periodically to appreciate the small wonders around us. The ride wasn’t rushed through and we learned a lot of cute jokes that had us all laughing throughout the ride. Although our daughter has ridden horses before we never had the pleasure of doing so, and we felt completely prepared and guided the entire time thanks to Bills attention to detail and effort to make us feel comfortable. We most definitely will be back again to ride and we can proudly say we earned our sticker!

Awesome experience!!! Bill was very personable and funny. Incredible scenery! Highly recommended! Thank you!!

The Best time! Beautiful scenery! Lots of laughs, and it was so relaxing to be outside going on the trail! Bill has lots of jokes and he enjoys what he is doing! Would definitely recommend and can’t wait to go again!

Very fun ride through the woods, lake and mountains. He said jokes and made sure we were being taken care of and safe!

We did 1.5-hour ride with Bill. It's the perfect activity to get away from traffic and electronics. It was an awesome mother-daughter time. I highly recommended.

My friends and I an amazing time here! Bill was extremely nice and fun. Highly recommend this experience! :)

Bill is an excellent guide and very family orientated.
My 2 grandchildren ages 7 and 10 had never been on a horse before. They did great with the calm horses, bill put them on.
I would highly recommend this small family business.
He also went above and beyond to help make this outing happen st the lady minute before I flew back to boston 👍🏻👍🏻👍🏻👍🏻👍🏻

Great Ranch! Fantastic Staff! With attention to detail and safety!! Horses were well trained and well maintained and taken care of. Scenic trails and varied terrain. Would highly recommend to everyone! Fun! Fun! Fun! WELL DONE!!!

My friend and I had a wonderful time! Bill is a great guy and the ride was lovely, I enjoyed it very much. Highly recommend!

My wife loves to ride, and she's good at it. I don't like to ride and predictably, I'm not very good at it. But I go along. My most recent go-along occurred at the Rocking S. I was prepared. I expected half-dead horses using dirty, busted tack, mounds of manure, a mute guide, and awful trails. That's the usual. Not usual: Good-tempered horses, in great shape. Tack that was clean and operable. Excellent trails with marvelous views. and Bill, the owner and guide: safety-conscious, joke filled, guiding expert, explanatory, and just about everything you could ever want in a local trail boss. If you're ready for a ride, I cannot think of a better facility or a better guide. Well done!

It was a fantastic after horseback riding along the wooded trails, crossing streams, and just enjoying the beauty in that part of VA. Bill is a wonderful host—friendly & outgoing. It was a fun filled 1h30 of riding great horse!

What a delightful experience. We were in the Winchester area during Memorial Day weekend and my wife saw this place on Yelp. My daughter has never rode a horse before and she really wanted to do this. My wife and my 8 year old daughter have little to no horseback riding experience. No matter.... Bill and his wonderful daughter gave a a crash course on riding and the three of us city slickers were ready to go.

We booked a 90 minute trip that included lots of varied scenery and terrain, included two creek crossings and a few uphills and downhills. My daughter really loved all of the ups and downs! She thought it was like a living roller coaster (she tends to exaggerate-- but it was fun)!

The whole time the horses were very well behaved and very responsive to us despite us being complete novices.

And Bill is a character whose passion for corny dad jokes rivals mine! Hey Bill... if you are reading this review I got one for you. What makes a corny joke become a dad joke? When it becomes "apparent"!

Seriously, book this guy.

Very polite and fun. Always concerned for safety and well-being. Animals were very well behaved. Bill and his jokes made the experience incredible. Ask him to tell you about the fish and the concrete wall joke!

Everything was above expectations! Bill was great tour guide. This was our first time but still we had a quick adaptation.

We had a blast! Bill kept us entertained with jokes along the ride as we rode through beautiful terrains and even a river crossing! Can’t wait to go back. :)

The Lazy S Ranch is an ideal spot for a scenic, relaxed horseback ride . This spring our grandchildren aged 8 and 11 rode with safety-conscious , entertaining Wrangler Bill through woods and hills, even fording a stream.

This was a great day reminicing about how simple life used to be before we were all 'connected'. Great host who took a lot of time to teach my two kids who were novices. Rode up and down wooded trails, through streams, over bridges, over the hills and through the woods although we didn't find grandmothers house (for those of you old enough to recall the song)! Call a few days ahead as this is run by a father/daughter duo so they aren't sitting by the phones, they our out helping others enjoy nature via horseback!

Beautiful scenery, blue skies, great horses, in this case, icing on the cake

My girlfriend was once an avid rider, but after a horseback accident that resulted in a broken nose and dislocated hip, she became so fearful of horses, she never rode again

Now, 25 years later, I persuaded to give it a another shot. She reluctantly did

We arrived about 45 minutes early. Bill was on ride with other customers and, while we waited, we took in the scenery, played with a couple of amazingly friendly cats, and enjoyed each other's company

When Bill arrived, knowing she was an experienced rider, put her on a more active horse and quickly shifted his focus on to me. As she waited, my girlfriend began to panic, the horse picked up on this and began to challenge her instructions

Bill quickly picked up on this and switched her to a more docile horse. A few times during the ride, she let me know that she was too nervous and wanted to cut the ride short, and at one point even I had given up, but Bill didn't. He calmed her down, coached her, guided her, and was extremely patient. I think he realized the importance of what he was doing... helping a person overcome their fear and acknowledging that the difference between her riding again or not in the future would come down to what happened on that day.

About 90 minutes later, we got back to the ranch, and she was smiling brighter than I have ever seen. After posting the pictures on Facebook, many commented on how they thought she'd never ride again. She did... and she will... thanks to Bill

Bill is a great tour guide, very knowledgeable, and entertaining. Best trail ride I've been on on the east coast. Horses are well kept and trained. Highly recommend for a fun day experience.

My wife and I stopped by on our vacation in Virginia. We called to make the reservation, and from the first conversation was very impressed with the owner, Bill. We did have to leave a message, as he was out cutting down some invasive plants that had sprouted up, and he returned our call promptly. Despite my wife and I's limited experience riding horses (meaning, zero), he was incredibly helpful and went through a full orientation on how to ride. We were blessed with a beautiful day, and had a great time riding the trails near the ranch. My wife loved trading jokes with Bill, who was full of great humor. Bill is a great guy who is fun to talk to, and very knowledgable. The horses were beautiful and very calm, and seemed to enjoy the trail as much as we did.

Tips:
-You MUST make a reservation ahead of time. He is unable to accommodate walk-ins due to the busy schedule.
-Regarding the proceeding one star review, the ranch is very much operational. Our understanding is that, as Bill is currently the sole employee due to cutbacks during COVID, he temporarily had to shut down the ranch for a few weeks due to some health issues, which are now, thankfully, resolved.
-Wear long pants for the ride, as you may scrape into some branches.
-There is a nearby sign on the trail that Bigfoot is on the prowl in the area... while we did not get to see the legendary Sasquatch, Bill did mention that he often sees wildlife when going on the trail with riders. Keep a look out!

This was without a doubt the best trail ride I've ever experienced! Bill, the owner and guide, gave us a variety of trail riding adventures, was very thorough in explaining what to do in different situations, and was entertaining the entire time! It's great for couples and families! So much fun! And Haley, his daughter, was so nice and helpful. Go see for yourself! We are definitely going back!

My husband and I just finished a wonderful anniversary afternoon of trail riding and lunch at Alesatian (recommended by Bill and a great find for sure). We've done a couple trail rides in the past and this was by far the best. Lovely trail through the woods and he even extended the ride since there wasn't a group right after. Great experience and we will definitely be back!!

My husband and I went to Rocking S Ranch in Winchester and rode the trails with Bill and we would highly recommend going if you are in town! The horses are very well trained and easy to ride and Bill is soo friendly and helpful (for my husband who has little to no experience it was perfect!). To add on to the experience Bill kept us laughing the whole time and took a ton of great pictures for us!!

I took my daughter to the Rocking S Ranch as a surprise for her 6th Birthday. She is really into horses but other than pony rides she hasn’t done any riding. I called Bill and he said he’d be able to accommodate us. He provided us with a day that I’m sure she and I will never forget. She has been telling people that it was “the best birthday trip ever.” Bill is a nice guy to be around, his trails are great, and his horses are even better. My daughter already said she wants to go back again, and my wife said she’s coming on the next one too!

This was our first visit with Bill and friends. What a wonderful way to spend a Sunday afternoon. The horses were very well behaved and friendly . Bill was a wealth of local knowledge. He even had local dinner recommendations. We are already planning our return trip.

We had a great time here at Rocking S Ranch! We rarely get away for date days because we have 4 kiddos. Bill was very accommodating and managed to get us in on the day we got a sitter even with such late notice. The horses were great and Bill gave a great tour, filled with jokes and friendly chatter. The trails were really nice and we had such a great time! Would definitely go back again!

I am a first time rider and my wife is a life long rider and we both loved it. The horses were obviously well taken care of. The owners are great people who made the experience that much better.

Wonderful day spent at Rockin S Ranch. Everything was great and thanks to Bill for making sure we had a fun time! The trail and horses were beautiful.

This was a great experience! Bill (our guide and the owner) is hilarious and knowledgeable. The area is beautiful and the ride is exciting. The horses were awesome and good for even beginning riders. Bring your friends!

Had a great time. Very personable and funny. Enjoyed the ride. Horses were gentle and easy to control.
To bad I can’t add a photo, the site won’t let me.

We had an amazing day. Bill is the real deal with true western horses. The trails were fantastic. Crossed creeks and climbed hills. Grab your boots and saddle up!

Bill is running a top-rate riding experience at Rocking S.

It starts with a quick orientation for how to handle his horses. He keeps it entertaining for everyone along the ride with family-friendly jokes and plenty of stunning views. Crossing creeks, ducking around trail corners, taking in the expansive mountains, and much more - this is a true riding experience.

Everyone is responsible for driving their own horse, we felt very safe with the three kids (ages 6-13) with us, and those of us who are more experienced didn't feel micromanaged. The horses are well-cared for as well, which is important to us. We got the full ride time also, which made us super happy. As the camera person, I usually am not in any of our photos, but Bill graciously offered to take tons of amazing photos of all of us in action.

This is definitely a 5-star experience and I highly recommend anyone who is a decent, horse-loving person to take this adventure. You won't regret it.

Great experience for our family. Bill is super friendly and accommodating. It was a great trip for kids (ages 9 and 10). We will be back!

Our family ride at the Rocking S Ranch was absolutely fantastic! Bill was an amazing guide and host, took lots of great pictures if our family, and was incredibly patient with our novice riders. Following our ride, Bill gave us fantastic recommendations for things to do and places to eat in Winchester. Then, he went way above and beyond and called ahead to our hotel and restaurants to let them know that we were on our way. We look forward to going back again!

I booked a 1.5 hour trail ride for my boyfriend and I to celebrate his birthday. We had a great time with Bill and really enjoyed our ride. The horses are very well trained and well maintained. We are super pleased with our experience. We have told our friends and family about it. They are really interested in going on horseback riding as well. So, we are definitely planning to return soon. I would say that just be patient with him returning your phone calls because he doesn't have anyone helping him right now. I suggest you call 7 days in advance. Anything more than he said he wouldn't book since he needs to know how the weather is going to be for that day. Just leave a voicemail and he will surely return your call. I highly recommend this place.

For my birthday this past weekend, we decided to go to virginia and tour the state from one end to the other. I looked up different places to go to, and this was one of the most highly recommended places to go to for horseback trail riding. Bill did not disappoint with the deliverance of the experience. Starts off with a more comfortable feel to finally getting into the woods. The horses are all very tame and bill was very informational as well as delivering terrible dad jokes haha.

The thing I loved the most about the whole experience is that my boyfriend is from Camden and strictly raised in a city setting. He was fully against getting onto the back of a horse while I was raised around farms. After we got back, we were driving and he was talking about how he wants to do it again and how the whole thing was incredible.

Would highly recommend rocking s ranch to anyone who's interested in giving it a try and is in the area. 10/10 would do it again. Thank you Bill for making my birthday a memorable one!

Bill was great! The girls had a wonderful first time riding experience. Nice variety in the trail taken. Loads of fun for everyone

We came to old town Winchester for a weekend get away- found Rocking S Ranch on TripAdvisor & left a voicemail, asking if there was any availability during our stay. Bill called the next day with plenty of availability to accommodate us. We went on a Saturday 1PM & had the best time. The horses were calm & the views were gorgeous. Bill also took many great pictures of the both of us, which was greatly appreciated. This was the highlight of our trip & we couldn’t recommend this activity more.

He is an extremely kind man, who loves his daughters, & does an incredible job making people smile & laugh with his jokes & friendly nature. He recommended other restaurants in Winchester- which were also high quality.

We would love to come back before he closes up shop.
Wishing him, his family, & horses all the best.

Fantastic experience all around! Bill was very enthusiastic throughout the entire tour. Filled my anniversary with many jokes and a ton of laughter! 10/10 would recommend to anyone and everyone looking to go horseback riding!

We had a awesome time! Great place to go whether you’re a beginner or an experienced rider. Bill is a great guide and has lots of jokes for you! We will definitely be back.

Our beautiful afternoon ride was amazing! Bill is real-life cowboy and expert horseman. Having had no experience riding, he quickly put me at ease. Highly recommend Rocking S Ranch!!!

In lieu of a birthday party, I bring my daughter (now 10) and her choice of friend to Rocking S Ranch. This was our second year riding with Bill and it was even better than the first! I think this will be a tradition for years to come. Definately recommend Rockin S Ranch for beginners and novices alike.

I loved the experience. My 6 year old even rode, and had a blast. The scenery is beautiful, and the horses are so well trained. Best part of our trip. Bring cash to tip!

Took the 90 minute ride in December on a birthday trip. Bill, the owner, is a character. Be prepared for truly dreadful dad jokes on your ride. It's a small ranch, so think port o potty, small stable, and personal service. That means you may wait a while if the ride before you runs over, but Bill won't cut anyone short. He even gave my husband gloves since he didn't bring any and it got really cold at the top of the hills. I ride, my husband does not, and even though parts were challenging for him (some steep hills both up and down, riding through water, navigating through trees), he had an excellent time and the horses were very well behaved. Nice touch is Bill takes one of your phones at the beginning and takes shots of you and the scenery along the way so you don't have to worry about dropping your phone while riding and you get lots of shots with your entire party in them. Highlight of our trip, would definitely return.

We picked Rockin S Ranch for a family trail ride with kids ranging from 8 to 14. We are all beginners and we all had a really great time. From crossing streams, riding ridgelines, negotiating hills, and navigating forested big foot country, Rocking S exceeded our expectations in every way. Bill provided outstanding service and we hope to be back soon. Thank you!

My husband and I came here for our 1 year anniversary and I absolutely loved it! Bill was very down to earth and a gave a great tour.

We were so excited to GO BACK to Rocking S after all this COVID crap, and what a great outside thing to do for my mom's 82nd birthday. It was a wonderful ride, safe, fun, and your host will keep you in stitches with his jokes! From teen to grandma, anyone can ride! I can't recommend them enough...so book as soon as you can because I figure as people start to venture out, they will be a bit hard pressed to meet the demand. We stopped at a winery to wrap the day as well, so thank you Rocking S for a perfect day. See you again in the future!

Bill, the owner, was very friendly and entertained us throughout our adventure with jokes and local stories, and sharing how proud he was of his daughters. He is very safety conscious for both humans and the horses. The horses were docile, our party was very inexperienced and still had a smooth, fun ride. We had a wonderful time and have many photos to show for it! Would absolutely come back if we were in the area again.

My wife and I went for the trail ride with Bill on a beautiful day in Winchester. Both of us being beginners, Bill made us feel comfortable from beginning to end. Once on the trail, we really enjoyed the ride and scenery. When in the area, we’ll sure to be back to Rocking S for another enjoyable day.

My boyfriend and I had such an amazing experience. The owner, Bill, was very entertaining. He suggested other things to do in the area. We had lots of fun. This is a must do when visiting the area. I suggest making a reservation in advance. The slots fill up very quickly.

This was such a great experience and the guy was so nice and horses well trained. We went dor my sisters birthday and i dont think we could have done anything better. 👍

I booked a ride a week in advance for my husband and I while planning a visit to Winchester. Although we haven’t ridden in years, Bill made sure that we were safe and comfortable. Throughout the ride, Bill pointed out native trees and told corny jokes. He even took pics of us, using our phones, to commemorate the experience. It was a good time and relaxing. Totally recommend 100%.

Rocking S Ranch is a small family owned ranch. You do need to call ahead and make reservations. But, the ride was well worth the wait. Bill, the owner, only takes out one party at a time. We were only a party of two and he easily could have put us in with another group. But, he strongly believes in giving his riders a very personal experience. He took my phone from me and snapped pictures of my husband and I throughout our ride, which included beautiful meadows, up hills to beautiful vistas and downhill through forests. He talked to us about the different plants we were seeing and some of the history of the area. If you are looking for a great trail riding experience, this is it! (And Bill is great with new riders and those with more experience.

It had been a year or so since my husband and I had been horseback riding (Red Rock Canyon, NV) and we wanted to find a place we could get away for an overnight excursion. My husband had worked Winchester several times in the past and had come across the Rocking S Ranch in trip advisor as a great place for a trail ride. He called and spoke with Bill (owner) and quickly found a time for a nice 90 minute ride for the two of us. Can’t say enough about Bill and his hospitality. Makes you feel right at home and at ease. We took Apache and Leroy out and thoroughly enjoyed the landscape, especially crossing the stream. We had a great time and plan to come back in early Fall to enjoy the foliage and a few more of Bill’s jokes. Give him a call, you won’t be disappointed.

We had a great time with Bill. My sons, 10 and 13, had never been on a horse before. After the first fifteen minutes, they were completely comfortable. The horses were well trained, but not so much that you felt you were on a merry go round-- nose to tail. The ride was just the right length and took us through meadows, creeks, and forest. I would highly recommend it. Bill also took a ton of photos with our camera throughout the ride which was really nice to have at the end of the ride.

It was amazing!!! Way beyond what I had anticipated, we arrived mid morning to the ranch from downtown Winchester. My wife and I both work in high stress environments, and we had been planning to do this for some time. After our arrival we were introduced to the other couple joining us. Bill and his daughter Haley, took the time to check the horses over as well as instruct us ( the riders) what to do, how to properly hold the reins and how to move in all directions. Once we were all loaded up and ready to ride Bill made sure to get some photos of us before leaving. The ride began at a nice slow and even pace while we and our horses became better aclImaged.He took us down the driveway and then down a dirt road and then I’ll think of the woods where we were able to see some great scenery and also be in the shade. From there we were able to cross two streams continue back through the woods and then back out to the road that we came on totaling all about an hour and a half. From there he took us up on two hunters Ridge above the creek that we were just riding through. All in all the trip was probably about an hour and 45 minutes and it was a great experience overall building his daughter wonderful my wife had a wonderful birthday and I would absolutely return and recommend it to anyone that I know. Bill and Haley thank you for making my wife’s birthday perfect!!!!!

Bill the owner was wonderful to work with to set up my family’s first ever trail ride. He was patient with my children ages 7&8. Sweet horses and Bill made us feel very comfortable. Woudl recommend him to anyone!

My 13 year old granddaughter suggested this activity to avoid another boring Sunday afternoon. My husband and I agreed to try it and oh what fun it was. Bill was a great host, teacher, entertainer and photographer. He made it a point to remember and use each of our names whenever communicating and that was a big indicator of the importance he placed on making everyone comfortable. He educated us on riding posture, handling the beautiful horses and the area's geography. The pace of the ride was perfect for our inexperienced family and we enjoyed the variety in the terrain. Bill's lighted hearted puns and great photography were the icing on the cake.

I would recommend the Rocking S Ranch trail ride for a family activity; Bill will definitely take good care of everyone.

Me and my little cousin went and had such a fun time! It was my first time riding a horse and it was amazing!

Had a great time this afternoon riding with Bill! Great guy, even better horses. If you are looking for a great time this is the place for you! I will definitely be booking with him again!

We had a wonderful time on our horse back riding adventure! We crossed streams, went up trails for a nice mountain view and walked underneath an arching canopy of trees (just like in the movies!). The horses are beautiful and we got lots of great photos. Thanks so much!!!

Had a great ride with Cowboy Bill. The horses were sweet and the trail was beautiful! He took pictures for us and entertained us with jokes and stories. We will definitely be back!

A must do when you visit Winchester! Bill will make you smile the entire ride with his wit and humor.

Had a great time with Bill, Hayley, and Harley. The trails were beautiful, Harley (The Horse) was easy to ride, and Bill was a great guide. I have around 50 photos to remember this experience thanks to Bill. Stop in and see them and enjoy some nature.

Tyler
Wisconsin

I had a fear of horses before going to visit this Ranch, we really appreciated Bill & all of his banter. Highly recommend.

My husband and I wanted our grandson to experience a trail ride. I was not sure what to expect, but Bill was great with my grandson. The trail was very diverse from going across the stream to thru some beautiful forest. Amazing views of the surrounding mountain ridges. Can’t wait to go again, worth every penny

Such a wonderful outfit! Family run and exceptionally great for the kids as well as the adults!!! Bill is a fun and informative guide while his daughter Haley is as sweet as can be! Could not have enjoyed it more!
You will want to come back again and again!

My husband (beginner) and myself (experienced) both had an amazing time. The horses are well taken care of and you can easily see that they are cared for with much love and attention. Bill was amazing in every way. He made sure to explain proper/safe riding in a very understandable way so that we/my husband were able to feel safe and confident in our ride and for those of us who are vertically challenged he even had a mounting block for us to make it so much nicer for us and the horses. He was very engaging in conversation and really made sure to see to us enjoying every part of our ride. He took pictures for us every step of the way without us even needing to ask for them and made it so we have many wonderful pictures. The horses were very well trained and very steady. Bill took us on a very nice and diverse ride. Crossing rivers, through the woods, under fallen trees up and down ridges and we even go to see big foots stomping grounds 😆. Its definitely something we will be doing again. It was well worth it.

My girlfriend and I went on a 2-hour trail ride with owner and guide Bill at the Rocking S Ranch a few weeks ago. I can't recommend this enough, whether for couples, families with children or friends. The horses are obviously well trained, very gentle and easy to handle. It's clear that rider safety is Bill's #1 priority. He is also a very entertaining guide, and very knowledgeable about the area. We had the good luck of arriving just after a snowfall, so the woods, ridges, stream crossings and views were beautiful. It's a rare opportunity to ride in the snow and we had a wonderful time for the right price. Highly recommended!

What a wonderful and memorable experience! Bill was the perfect guide. He kept my kids and I entertained all the way through. What a warm hearted guy. And ofcourse we were riding through beautiful Shenandoah countryside. Make no mistake, we’ll be back!

We had a great ride with Bill. Everyone - including 9 and 10 year olds - had a lot of fun on the ride. Especially liked the creek. Even got to see a black snake. Would definitely recommend.

Unique experience we loved how comfortable he made us feel highly recommend for even your first time like me , the horses were easy to ride they basically knew the way . It was a very peaceful ride

Son took me riding it was nice if a bit cold but Bill is a nice guy and his daughter is very helpful loved it.