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7 Day Aspen Summer Itinerary

View of Aspen in Summer
18 Jun 2024
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Outdoor Activities

Aspen’s natural beauty, cultural richness, luxury amenities, and variety of outdoor adventures make it an ideal summer destination. The moderate summer temperatures mean plenty of opportunities to enjoy the beautiful Colorado sunshine and the alpine scenery for which Aspen is renowned.

If you’re dreaming of spending your summer vacation here, we’ve compiled a sample itinerary that includes outdoor adventure, dining, and wellness to ensure you enjoy everything Aspen has to offer.

Day 1: Arrival and Exploration

Morning/Afternoon: Arrival
You have arrived! Check into your Aspen Square rental and enjoy full hotel-style services and amenities such as fully-equipped kitchens and your own private balcony with picturesque views. Once you are settled and you’ve had some recuperation time, put on your walking shoes. It’s time to explore downtown.

Downtown Aspen’s pedestrian mall has something for everyone. Whether you are a cultural enthusiast, a foodie, an art lover, or simply someone who loves to browse around town, you will surely enjoy Aspen’s refreshing mix of high-end boutiques, art galleries and unique local stores. Enjoy dinner at one of Aspen’s highly regarded downtown restaurants, like the Monarch or White House Tavern.

Day 2: Outdoor Activities

Morning: Hiking in Aspen
Abundant hiking and biking trails of all levels exist in the area around Aspen, which is surrounded by beautiful forests and natural trails. You can explore all of our Aspen hiking recommendations here.  If you prefer to enjoy nature in town on more leisurely trails, visit the John Denver Sanctuary for a picnic amongst the stunning gardens and rock sculptures celebrating one of Aspen’s most beloved residents. 

Evening: Sunset Dinner
Enjoy dining at the base of Aspen Mountain, across the street from Aspen Square,  with a sunset dinner at Ajax Tavern. The truffle fries are a great way to end the day!

Day 3: Culture and History

Morning: Art and Lunch
Aspen has a very lively art scene and many galleries for art enthusiasts to enjoy. Visit the Aspen Art Museum to see some contemporary art exhibitions, then grab lunch at their rooftop cafe. Alternatively, you can visit the Resnick Center for Herbert Bayer Studies, located on the grounds of the Aspen Institute, and view their latest exhibition, while learning about Bayer, an important figure in the early years of Aspen’s cultural development.

Afternoon: Walking Tour
Taking a guided walking tour of Aspen’s historical sites and scenes is a fun way to learn about our rich history. The Aspen Historical Society offers a variety of walking tours to educate visitors and residents about the area.

Evening: Theatre Aspen
Catch one of Theatre Aspen’s award-winning performances featuring the best of Broadway talent in musicals, plays, and more. 

Day 4: Luxury and Wellness

Morning: Spa Time
Book a day of relaxation at one of Aspen’s premier spas, such as RAKxa Wellness Spa at The St. Regis Aspen Resort, Yarrow at Hotel Jerome, O2 Spa, or the Spa at Viceroy Snowmass. Experience everything from a wellness massage, full-body exfoliation, or scalp treatment to manicures, facials, and other tailored organic treatments designed to restore balance and alleviate tension.

Afternoon & Evening: Fine Dining and Shopping
Spend your afternoon on a retail excursion in downtown Aspen's boutiques, where you can find designer goods and luxuries or local one-of-a-kind items. Then, enjoy dinner at one of Aspen’s many great restaurants.

Day 5: More Outdoor Adventures

Morning: Time on the Water
The Roaring Fork River and nearby lakes provide excellent opportunities for fly fishing. Breathe in the fresh air and observe the natural beauty and wildlife that populate the area. Learn more about fly fishing in Aspen.

Afternoon and Evening: Mountaintop Fun
Hitch a ride on the Silver Queen Gondola to the top of Aspen Mountain. Check out some of the fun activities on the mountain, including disc golf or live music on the weekends. Bring a picnic to eat outdoors while taking in the breathtaking views. You can also enjoy food purchased from the Sundeck.

Day 6: A Day Trip

Morning & Afternoon: Rafting in Glenwood Springs
Take a day trip to Glenwood Springs for a rafting adventure on the Colorado River. Be sure to come prepared with outdoor gear–hat, sunscreen, sunglasses and a sense of adventure!

Evening: Dinner in Aspen
Return to Aspen for a delicious dinner at a cozy spot like the Meat & Cheese Farm Shop for one of their delicious gourmet boards to share.

Day 7: Departure

Morning: Fuel Up
Grab a leisurely breakfast at Poppycock’s on your last day. Enjoy their famous pancakes or a benedict before heading out.

Afternoon: A Last Stroll Through Town
Head downtown, take a final stroll through the pedestrian malls to enjoy the scenery, and grab any last-minute memorabilia for your trip. 

Tips Before You Go


Aspen Square’s knowledgeable and friendly concierge staff are well-versed in every aspect of Aspen’s big-city amenities, from dining options and can’t-miss concerts to the latest boutiques and the trendiest new places to see and be seen. Our guests can begin organizing their stay by contacting our concierge before arrival. 

Pack Accordingly

Aspen summers are mild, with warmer temperatures during the day and frequent thunderstorms in the afternoon. However, if storms stick around, temperatures can dip significantly, and evenings can often become chilly. Be sure to pack a rain jacket and light layers to stay warm in the evenings. View our Aspen summer vacation packing list for more information.


Ensure that you allow enough time for your body to acclimate to the change in altitude, especially if you are coming from lower elevations (or sea level). Allow yourself time to acclimate, stay hydrated, and avoid overly strenuous activities on your first day.

Spend a Week in Aspen This Summer

Aspen is hard to beat when it comes to summer vacation destinations. With plenty of activities to do outside and the town’s vibrant cultural scene, there’s something for everyone. Get the most out of your summer in Aspen by choosing the perfect vacation rental.

When you choose Aspen Square condominium lodging, you get the benefit of hotel services combined with the comfort of home in a superb downtown Aspen location with easy access to the mountain, entertainment, and dining. 

Our condominium hotel combines luxury features such as well-equipped kitchens, wood-burning fireplaces, and private balconies, and the convenience of hotel services such as a front desk, concierge, bell staff, and daily housekeeping. 

Contact the concierge at Aspen Square to plan your family vacation this summer in Aspen. Call (970) 925-1000 and let us assist you!