72 Hours in Aspen: The Ultimate Winter Weekend Itinerary
Aspen is more than just a ski town—it’s a destination where breathtaking landscapes meet upscale charm, offering the perfect mix of adventure, culture, and relaxation. Whether you’re here for the powdery slopes, the gourmet dining, or simply the crisp mountain air, 72 hours in Aspen is enough to leave you refreshed and inspired. From sunrise hikes to après-ski indulgence, this guide will help you make the most of your short but sweet getaway to Aspen.
This guide is mostly for winter activities, but Aspen is also great in the summer time with lots of outdoor adventures like hiking or white water rafting. Note: If you are going for the winter activities and apres ski vibes, most places don’t open until mid December.
We found this out the hard way as we went end of November. Depending on how much snow Aspen gets, lifts don’t normally open until mid December. We actually got lucky and we were there for the season opener of the lifts (again lucky because normally this wouldn’t be until December). Keep this in mind when planning your winter getaway. Some of the restaurants you want to visit may not yet be open for the season.
Day 1
Day 1 you will likely arrive in Denver Airport unless you fly directly into Aspen. I don’t necessarily recommend flying into Aspen unless it’s your only option. It is a very small airport and often has delays. We flew into Denver from Chicago and rented a car and drove to Aspen, the road trip has beautiful scenery and cute towns to stop at along the way.
If you are driving I recommend stopping in Idaho Springs, it’s a cute little town at about the half way mark to Aspen. Stop by the Frothy Cup for some coffee and treat, an adorable coffee shop.
Hotel
- St. Regis: We stayed at the St Regis and it sure made our stay special. Located at the base of Aspen Mountain, offering an elegant blend of alpine charm and refined sophistication. Known for its impeccable service, lavish accommodations, and world-class amenities. I went to the gym and it was once of the nicest hotel gyms I’ve worked out in.
- The Little Nell: Aspen’s only five-star, five-diamond hotel, offering a sophisticated yet cozy retreat at the base of Aspen Mountain. Renowned for its ski-in/ski-out access, exceptional service, and luxurious accommodations, this boutique hotel is a favorite among discerning travelers. With award-winning dining, an extensive wine program, and exclusive adventures like off-road excursions and private ski experiences, The Little Nell delivers an unparalleled Aspen experience.
- Limelight Hotel: The Limelight Hotel Aspen offers a modern, relaxed vibe in the heart of downtown, featuring spacious rooms, a lively après-ski scene, and easy access to outdoor adventures.
Activities & Sights
- Snow Mass Village: Perfect for those who don’t ski or even those who do! Snow mass village is a great place to start your snow adventure with tubing, skiing, gondola rides and the alpine coaster. I recommend booking the coaster in advance as certain times can sell out.
- Shopping: If you’re into luxury shopping Aspen has many stores and boutiques to pop into to get away from the cold
Food
- White House Tavern: We went here for a casual dinner on our first night and omg. We absolutely loved it! I got the French Dip Au Jus, it has to be in the top 5 best sandwiches I’ve ever eaten in my life. The drinks were also so amazing, I got “The Crush” and it was the best cocktail I had on the trip. 100% must go
- Pine Creek Cookhouse: Located in a breathtaking alpine setting, perfect in the winter time when the only way to get to the restaurant by horse drawn carriage. Definitely make reservations way in advance.
- Cloud 9 Alpine Bistro:
Day 2
Activities & Sights
- Skiing/Snowboarding: If you came to Aspen to do some skiing or snowboarding, Aspen is famous for its four ski areas: Aspen Mountain, Aspen Highlands, Snowmass, and Buttermilk, offering world-class slopes for all skill levels.
- Silver Queen Gondola: If you don’t ski but still want to take in mountain breathtaking views, you can still take the Gondola up Aspen mountain and enjoy
- Aspen Art Museum: A great way to break up the day after a day of skiing or even from walking around the town. A cute art museum, with free admission and great mountain views.
Food
- French Alpine Bistro: This place is great for the alpine vibes and drinks. I wouldn’t go here for dinner
- Ajaxx: Located at the base of Aspen Mountain, this upscale yet casual spot is famous for its truffle fries, wagyu burgers, and vibrant outdoor patio scene. Perfect for people-watching and post-ski cocktails.
Day 3
Sights & Activities
- Snowmobiling: Snowmobiling is a thrill, I highly recommend to everyone who has never had the chance to try. It is a little scary at first but the guides are great at demonstrating. There are a couple of companies in Aspen to book but there are plenty of other companies who offer tours. We ended up going with Sage Outdoor Adventures a little outside of Aspen.
- Maroon Bells Snowshoeing: If skiing or snowmobiling aren’t your thing, you can take a stroll through Maroon Bells with beautiful scenery, a great way to spend an afternoon.
Food
- Sweet Coloradough: If you find yourself driving back to Denver needing a stop for a coffee, this place was AMAZING. The breakfast sandwiches, the donuts, ugh! Highly recommend making a pit stop here.
- Felix Roasting Co: If you’re in the town of Aspen this is a great place to stop for coffee or a snack.
- Clarks Oyster Bar: We had a great dinner here. Very fresh fish and sea food. It is a chain but they make it feel cozy and special with the ambiance.
Conclusion
After 72 hours in Aspen, you’ve experienced the perfect mix of adventure, luxury, and relaxation in one of the most breathtaking mountain destinations. Whether you carved through powdery slopes, explored scenic hiking trails, indulged in world-class dining, or soaked in the après-ski atmosphere, Aspen delivers an unforgettable escape. With its blend of outdoor thrills and refined charm, this vibrant town leaves a lasting impression—one that will have you dreaming of your next visit before you even leave. I LOVE winter getaways, they’ve become some of my favorite kinds of adventures. If you want more alpine adventures, check out my Switzerland blog here <3
