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How Long Should You Stay in Aspen, Colorado?

Aspen gondola
22 Apr 2024
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When it comes to determining how long you should stay in Aspen, the answer is complicated. In short, it all depends on what kind of vacation you are looking for, when you plan to visit, and how much you are willing to pack into your days. We find a week is ideal to take advantage of everything Aspen has to offer, but the truth is, you can still enjoy a long weekend here and make the most of it. 

Below are a few of our favorite must-see experiences you shouldn't miss during your visit, no matter how long you decide to stay.

Spending a Long Weekend in Aspen

If you are short on time, a long weekend in Aspen will still be enough to enjoy the area's offerings. This three-day itinerary offers ideas to help you fit all of the best attractions into one quick trip!

  • Rent a bike or e-bike and ride around downtown, or venture out on one of the nearby trails. 
  • Explore downtown Aspen’s charming streets. Check out the many boutique shops or galleries that punctuate the downtown area.
  • Visit the iconic Maroon Bells and get out for a hike with six pet-friendly trails and majestic scenery. 
  • Hit the slopes. Winter is Aspen’s time to shine. With four mountains and a mix of terrain, there’s plenty of skiing and snowboarding to be had.
  • Enjoy the local cuisine! Aspen is renowned for its restaurant scene, with culinary flavors to suit any palate. Dine at one of our many distinguished restaurants.  
  • Check out Aspen’s legendary nightlife. There's something to appeal to everyone from craft beer to craft cocktails, live music, and DJs. 

Spending a Week in Aspen

Whether you are looking to explore art, nature, or local cuisine, a week in Aspen promises to be extraordinary and brimming with things to do. 

  • Experience one of Aspen’s many unique events, such as the Winter X-Games at Buttermilk or Wintersköl on Aspen Mountain. If you plan to visit in summer, more festivities are available, including the FOOD & WINE Classic, the Aspen Music Festival and School, and the Aspen Ideas Festival. Check the events calendar for a list of happenings year-round.
  • Catch a summer show at Theatre Aspen or a free concert at the Snowmass Free Concert Series.
  • Stroll the Saturday Market downtown for local produce, fresh flowers, and artisan products. Open from 8:30 am–2 pm every Saturday from mid-June through mid-October.
  • Visit the John Denver Sanctuary for a family picnic or to take in the tranquility of the lush gardens.
  • Explore all four mountains for different ski and snowboard terrain and something for all ski levels.
  • Pay a visit to the Aspen Nordic Center just outside of town and rent cross-country skis or snowshoes, take a lesson, and check out more than 60 miles of free trails.
  • Take a snowcat ride into the backcountry with a personal guide from Aspen Powder Tours. Check out the open bowls, snow-covered meadows, and quiet glades around Aspen Mountain.

Spending More Than a Week in Aspen

Staying longer? Use Aspen as your home base and explore the area, or dive deeper into exploring the town’s offerings.

  • Embark on a scenic ride from Aspen to Woody Creek Tavern, following the Roaring Fork River. Stop and have lunch at this iconic spot associated with the legendary Hunter S. Thompson. 
  • Take a day trip to one of the many nearby destinations around Aspen.
  • Spend another evening finding more of the area’s best places to take in a show. Many of the local venues are near one another, so hopping from place to place is easy.
  • Try a new restaurant! There are sure to be plenty that you still haven’t visited. Find a small, locally owned place with the charm and ambiance only found in Aspen. 
  • Purchase a ticket for the Silver Queen Gondola and head up to the summit of Ajax to view the beauty of the mountain ranges. Go hiking, enjoy a game of disc golf, lawn games, or other fun activities at the top.
  • Drive up to Independence Pass and take in the awe-inspiring views.
  • Hike the Grottos Trail to see the breathtaking waterfalls and explore the ice caves.
  • Take a break. Enjoy being away from the hustle and bustle, breathing that fresh alpine air, and taking life at a more leisurely pace.

Planning Your Aspen Vacation

No matter how long you plan to stay, staying downtown at Aspen Square allows you to get the most out of your Aspen vacation. Enjoy the convenience of walking to restaurants, events, fun nightlife, and boutique shopping, as well as easy access to the main free skier bus terminal, which will take you to Buttermilk, Snowmass, or Aspen Highlands, with the Aspen Mountain gondola situated only one block away.

Explore our Aspen condo rentals to view our available rentals and plan your vacation. Contact Aspen Square’s Reservations desk ( if you need assistance booking your stay with us. 

Guests can also contact our concierge staff ( for advice and assistance in choosing activities, purchasing event tickets, or making restaurant reservations. We hope to see you soon!