Portland and Ogunquit Trip Late September

Question

I am in the preliminary planning stages for a 6-7 night trip in mid to late September. We plan to fly to Portland and stay for 3 nights then drive to a different coastal destination for 3 more nights. I have chosen Ogunquit for our beach destination, but am open to other choices within a 2 hour drive. We are from Colorado, so get plenty of outdoor recreation at home. This trip is for enjoying the beautiful coast, the food, and a relaxed pace of puttering around.

Thanks in advance for recommendations. We are somewhat flexible on dates, but want to avoid the summer crowds and usually travel during the week.

Answer

Your trip sounds lovely, and late September is a fantastic time to visit Maine—just after the summer crowds have thinned out, but before the crisp fall weather fully sets in. You’ve made a great choice with Portland, and Ogunquit is a charming beach destination, but I’ll also offer a few alternatives within a two-hour drive that might be worth considering.

Here’s a suggested itinerary for your trip along the Maine coast, focusing on a relaxed pace, local food, and enjoying the scenery:

Portland (3 nights): Portland is a great base for your first three nights. Known for its vibrant food scene, historic Old Port district, and coastal beauty, you’ll have plenty to explore without feeling rushed.

Things to do:
- Explore the Old Port district with its cobblestone streets, boutique shops, and waterfront views.
- Visit Portland Head Light, one of Maine’s most iconic lighthouses, located in Fort Williams Park.
- Stroll around the Eastern Promenade for beautiful coastal views and a relaxing walk along the water.
- If you enjoy seafood, try the famous Eventide Oyster Co. or J’s Oyster for some of the freshest seafood in the area.
- For a more leisurely day, take a ferry out to one of the nearby islands like Peaks Island for a day of hiking or cycling.
Food and Drinks: Portland is a food lover's dream. Be sure to visit Central Provisions for small plates or Fore Street for farm-to-table dining. For casual drinks, head to Liquid Riot Bottling Co. or Bunker Brewing for local craft beer.

Ogunquit (3 nights): Ogunquit is a lovely choice for a relaxing beach destination. It has a laid-back vibe and beautiful coastal scenery, with lots of outdoor activities to enjoy, but it can get crowded in summer, so late September will be perfect.

Things to do:
- Walk the Marginal Way, a 1.25-mile scenic cliff walk that offers breathtaking ocean views.
- Visit Ogunquit Beach, which is expansive and beautiful, perfect for a peaceful stroll or lounging on the sand.
- Explore the charming downtown area for boutique shopping, art galleries, and cafes.
- If you're up for a hike, try the Mount Agamenticus area for panoramic views of the coast and surrounding landscapes.
Food and Drinks:
- Enjoy dinner at The Lobster Shack for some of the best lobster rolls or head to Arrows for fine dining.
- If you’re into casual beachside dining, check out Beach Plum Farm for a relaxed atmosphere and great food.

Alternative Coastal Destinations: While Ogunquit is a fantastic option, here are a few other coastal towns within a 2-hour drive of Portland that offer a similar vibe with their own unique charm.

Kennebunkport (1 hour from Portland): A picturesque town with lovely beaches, excellent shopping, and a great food scene. You can enjoy a scenic walk along Goose Rocks Beach or visit the Walker’s Point area where George H.W. Bush’s family compound is located.
Camden (1.5 hours from Portland): Known for its scenic harbor, Camden offers breathtaking views of the coastline and mountains. Explore the town, visit Camden Hills State Park, or take a sailing trip in the harbor. Camden is also home to great food spots like Fresh and The Smiling Cow.
Boothbay Harbor (1.5-2 hours from Portland): A lovely coastal town with a quaint downtown, a vibrant harbor, and scenic gardens at Coastal Maine Botanical Gardens. This is also a great spot for a relaxing boat tour of the harbor or nearby islands.

Relaxing Activities: Since you’re looking to enjoy the beautiful coast at a relaxed pace, be sure to spend time simply enjoying the views from a quiet beach or a cozy café with ocean views. Taking scenic drives along the coast, such as the Scenic Route 1, is also a great way to soak in the natural beauty of the area.

Overall, your itinerary sounds like a perfect combination of relaxation, outdoor exploration, and local culture. Whether you stay in Ogunquit or choose an alternative destination like Kennebunkport or Camden, you’ll find plenty of opportunities to enjoy Maine’s coastal beauty and delicious food. Late September will be a fantastic time to experience all of this without the summer crowds.

Portland and Ogunquit Trip Late September

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