Aspen Winter Bucket List

Catch first tracks on Ajax with Aspen Snowmass. Whether you're carving fresh corduroy or gliding down fluffy powder, first tracks gives strong to intermediate riders the chance to get first tracks on whatever conditions the day brings. Led by an experienced pro, get a head start on your ski day with one guided run before the lifts open to the public (valid ticket or season pass and first tracks reservations are required).

After a run or two, dig into the oatmeal pancakes at Bonnie’s. On bluebird days, catch a few morning rays on the deck or settle in by the window and watch the snow flakes and skiers fly by. Trust us, it’s worth the ski break.

Discover the many hidden shrines on Aspen Mountain. From tributes to musicians to remembering legendary locals and fallen friends, keep your eyes peeled for a glimpse into the past.

Hike the Highland Bowl, known for stunning mountain views and stellar steeps. Before you hike the bowl, make sure you know how to ski the Highland Bowl like a local. If you don't already have one, you can purchase a ski strap for the hike either at Aspen Highlands patrol headquarters or from a local outdoor retailer in town. We recommend a few warm-up laps before the big hike. Aspen Highlands favorites include Thunderbowl, Steeplechase, and Deep Temerity. Highland Bowl hike is not for everyone. Even when choosing to utilize the snowcat, which can take you part of the way up the ridge, you still must hike to an elevation of 12,392 feet to ski the double black diamond – experts-only terrain. Risks include death. Be prepared and know before you go.

Dance the night away to live music at Belly Up, sway to the sounds of smooth jazz at the newly opened Paul JAS Center, or catch a performance at the historic Wheeler Opera House. Explore the exciting lineup of events and arts and culture this season.

Watch the pros catch air and push the limits of their sport at X Games Aspen. From action-packed competitions to a lineup of DJs, experience the excitement at Buttermilk Mountain from January 23-25, 2026.

Race your friends to the NASTAR finish line on Aspen Mountain.

Indulge in après ski. Not sure where to go? Check out our guide to après ski in Aspen.

Hit the skintrack. Uphill skiing has been gaining immense popularity in Aspen. Besides a rewarding workout, uphillers enjoy breathtaking mountain views and a well-earned run back to town. For a list of rules and regulations, click here.

Take a horse-drawn sleigh ride during the day or under the stars to Pine Creek Cookhouse for lunch or dinner; check out these additional adventure dining options in Aspen.

After a full day of adventures, unwind with a night on the town and refuel with a delicious dinner.

Looking for more fun in Aspen? From the thriving arts and culture scene to the downtown pedestrian malls full of art galleries, shops, and a range of restaurants, explore all that Aspen has to offer.

First tracks on Ajax: Rise and shine! The early bird gets the powder here in Aspen! Guests can sign up for first tracks with Aspen Snowmass daily starting in early December. Skiers and boarders will meet their guide at the base of the gondola at 8 a.m. for a tour of the best powder on the mountain that day. Space is limited and interested parties must sign up in advance. *First Tracks on Aspen Mountain is offered to those in Private Lessons/Guided Experiences with the Ski & Snowboard Schools and to those guests staying in one of our Aspen Skiing Company lodging properties.

Bonnie’s breakfast: After enjoying a couple of first track runs, head down to mid mountain for breakfast at Bonnie’s. On a bluebird day, the best seats are outside on the deck where you can watch skiers pass by next to Ajax Express lift. We recommend the oatmeal pancakes, but if you’re not ready to head in just yet, opt for lunch instead and make sure to save room for Bonnie’s famous apple strudel.

Head to Aspen Highlands & hike the Highland Bowl: If you actually did get in some ski conditioning before the season, try tackling multiple mountains in one day. Thankfully, RFTA offers free transportation to all four mountains. The bus ride from downtown Aspen to Aspen Highlands is around ten minutes; just enough time to sit down in between runs and catch your breath. Once you arrive to Highlands, head straight up and towards the Highland Bowl, where you’ll find some of the most intense skiing in Colorado. Skiers and boarders hike about 30-45 minutes to the top, with 2,500-vertical-foot descents down pitches as steep as 45 degrees.

Soak in the W Aspen rooftop hot tub: There is truly nothing better than a hot tub after a long day on the mountain. Luckily, the W Aspen’s hot tub and heated pool are open to the public (as long as you’re having a drink or snack). The living room at the W is definitely on the top of the list for best après in Aspen with DJ’s frequenting rolling in and out and warm outdoor fire-pits to keep you warm as you enjoy some tasty post-ski fare.

Out to dinner: With 60 restaurants and bars in Aspen, it can be hard to choose where to dine in town. Searching for something easy and reasonably priced? Head to Public House or White House Tavern. Want something a little more fancy? Try Matsuhisa, Cache Cache or Steakhouse 316. For a complete list of Aspen restaurants and bars click here

….Sleep and repeat! Or check out Snowmass or head to Buttermilk to hit up their parks and pipe. Not a skier? Discover all of the other off mountain winter recreation to be had in Aspen.

Tag us in your winter adventures on @AspenCo for a chance to be featured on our page and website!