My wife and I will be making our first visit to Colorado in late August. The only set date is 8/28 to see Sierra Ferrell at Red Rocks. We have max flexibility as to where we fly in/out of, and although we're not young don't have any physical limitations. We would like to see a lot without biting off too much. I can either start or end the trip with the concert.
One possibility is flying into Aspen and out of Colorado Springs, with a night or two in several spots.
Another idea would be to fly into Durango to see Mesa Verdo, then up to Montrose for the Black Canyon of the Gunnison, then to Salida, up past Breckinridge to Red Rocks, then finish with a day or two in Colorado Springs.
Planning 7–10 days in Colorado with a fixed Red Rocks date gives you a perfect chance to see several of the state’s most iconic regions without rushing. Since you’re open to flying into or out of different airports, you can build a route that naturally flows from mountains to canyons to cities. Below is a detailed, practical breakdown of two excellent itinerary structures plus variations to help you decide.
Your two draft ideas are both strong, and each offers a mix of landscapes, culture, and manageable driving times. The key is to organize the trip so you’re not backtracking and you give yourself recovery time before and after the Red Rocks show.
Below is a detailed suggestion for each option, with daily pacing and recommended stops.
OPTION 1: Aspen ➜ Central Mountains ➜ Denver & Red Rocks ➜ Colorado Springs (Moderate pace, mountain-focused)
This route gives you classic Colorado mountain towns, shorter drives, and excellent food/scenery, ending with the concert and a relaxing finale around Colorado Springs.
This itinerary is great if you want easier travel days, beautiful alpine scenery, and a mix of adventure and relaxation. It avoids the longer drives of the southwestern portion of the state.
OPTION 2: Durango ➜ Mesa Verde ➜ Montrose ➜ Salida ➜ Breckenridge ➜ Red Rocks ➜ Colorado Springs (More driving, more national-park-quality scenery)
This version covers Colorado’s spectacular southwestern region—which many consider the most dramatic part of the state—but involves longer drives. It’s excellent for people who enjoy scenic roads and national park landscapes.
This itinerary is best for those wanting Mesa Verde/Black Canyon highlights and don’t mind the extra miles. Late August weather is great for the southwest.
WHICH OPTION IS “BETTER”?
If you want a hybrid option, consider flying into Montrose (near Black Canyon), looping through Ouray/Silverton, then continuing north toward Salida, Breckenridge, and Red Rocks. This still gives you high-impact beauty with slightly less driving than Durango/Mesa Verde.