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Aspen Ski Trip Itinerary - 7 Days in Aspen

Powder Skiing
18 Jan 2024
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Outdoor Activities


Welcome! You have arrived in Aspen and are welcomed by visions of a wintry wonderland with iconic mountain views and crisp, clean alpine air. We recommend giving yourself a little time to acclimate to the higher altitude by making your first day leisurely.

If you are a guest of Aspen Square, check-in and get comfy next to the wood-burning fireplace. Guests at Aspen Square enjoy an idyllic downtown location with easy, unbeatable access to everything, as well as hotel-style services and amenities.

Stroll the pedestrian mall once you are ready to check out the town. Check out the boutiques and restaurants, and decide on a place for dinner. Head to the White House Tavern for a quaint, cozy atmosphere tucked into a Gothic-style Victorian house, with a menu chock-full of tasty sandwiches and hearty salads. Enjoy the French dip piled high with prime rib on a hearty roll, or dive into a hearty kale salad with rotisserie chicken and a delectable peanut dressing. 

It’s time to head back for a great night of sleep! Tomorrow will be a busy one.


Kick off your first day on the slopes! If it’s been a minute, it’s a good idea to pace yourself since the week is just starting. Snowmass is the perfect mountain to get comfortable or maybe even take a ski or snowboard lesson as a refresher if need be. But first things first, make sure to fuel up so you have some calories to burn! Grab a quick, delicious breakfast and an amazing cup of coffee at Fuel Cafe before you head up to the mountain.

Take a breather from your ski morning and grab lunch at Elk Camp while cozying up next to the fireplace. You can choose from burgers, rotisserie, panini, hand-tossed pizzas, and sweet treats from the bakery. It’s the perfect spot for a quick lunch before you head back out to ski.

Once you feel like you’ve mastered Snowmass, head back to your Aspen Square condo to relax before you go out for a delicious dinner at Meat & Cheese. Try one of their scrumptious boards, like the rotisserie chicken board, with a glass of wine from their great selection, and see why locals love it here.


Start your third day in Aspen with breakfast at the Aspen favorite Paradise Cafe. Grab a chai tea latte and one of their famous breakfast burritos before starting your ski day.

Head towards the Silver Queen Gondola to go up Aspen Mountain (AJAX), and check out the new Hero’s terrain and high-speed quad. With 153 newly added acres on the upper eastern aspect of the mountain, challenge yourself to some of the best quad-burning runs in the country! After a morning of skiing, hit up the gondola and head over to the Sundeck for lunch and amazing mountain views.

After you wrap up a fun day on AJAX, take in the après scene at Ajax Tavern. Enjoy some truffle fries and a local brew while soaking in the fresh mountain air and sunshine and watching skiers and riders descend the hill.

Round off your day with delectable fresh sushi and sake at Matsuhisa. Don’t skip the chocolate molten lava cake for dessert!


Enjoy another day in Aspen by starting with some old-fashioned oatmeal pancakes or avocado toast at Poppycock’s for some morning energy, because today you will hit up the locals’ favorite, Aspen Highlands. Runs in Aspen Highlands range from easy to difficult, with the lower part of the mountain being easier while the upper is steeper. Advanced skiers will enjoy the steep bowls and runs through the airy woods and the crowning glory of Aspen Highlands, the infamous Highland Bowl. Regarded as a rite of passage for both locals and visitors, the strenuous hike to the top is worth it for some of the best runs in the world.

Visit Aspen’s Cloud Nine Bistro atop the Cloud Nine Lift for lunch and experience a slice of Switzerland. With fondue and raclette as well as steak tartare, caviar, and delectable daily specials, you’ll love the menu and the cozy European-style atmosphere. Please note that due to its popularity, reservations are required.

After a day at Aspen Highlands, it’s time to wind down and enjoy a delectable dinner of fine dining at PARC Aspen. Try the stuffed coq au vin with the Aspen donuts for dessert!


Wrap up your skiing days with another day at Aspen Mountain to challenge your ski skills and push yourself. Fuel up with a cortado and a veggie burrito from Unravel Coffee, then head up Aspen Mountain to find some amazing steeps and deeps. If you are looking to get away from the groomers, there are some great powder stashes that aren’t hard to find. The Dumps are a series of runs down former mine debris that form narrow descents through the trees. The Silver Queen Gondola allows you to see these perfectly spaced glades and open powder fields just off to the right as you ride up the mountain.

Head to Bonnie’s for lunch and sit on the two-tiered deck to catch some rays while resting your feet. Then, wrap up your day on the mountain, making the most of your remaining time by getting in as many turns as possible!

The Snow Lodge has a great après scene with tasty eats and drinks and live music courtesy of their ski music series. After enjoying what they offer, it’s time to return to your room and relax before an elegant dining experience at Element 47. Soak in the beautiful ambiance while sipping on a glass of wine from their extensive list, and marvel at all the skiing you’ve enjoyed over the past few days. We recommend one of the wagyu entrees to reward yourself!


After four days of skiing, it’s time to wind down with a relaxing day. Head to Mawa’s Kitchen for a leisurely, delectable breakfast and coffee. Pancake lovers will be in heaven with their fluffy goodness here, while benedict lovers won’t go wrong with any of the menu’s offerings.

Delve into some retail therapy as you peruse the many shops and boutiques. Head to Pitkin County Dry Goods for special finds, or browse the many luxury designer brands with stores here. 

Take advantage of the free admission to the Aspen Art Museum for one of their amazing contemporary art exhibits. While you are there, head up to the Rooftop Cafe for a delicious farm-to-table lunch and cappuccino. 

After relaxing in your Aspen Square condo, it’s time to head out for dinner. Take a horse-drawn sleigh and enjoy the stunning winter atmosphere as you head to Pine Creek Cookhouse for an unforgettable winter dinner with options like duck breast or elk strip steak. 


It's time to wrap things up on your final day in Aspen. Before you leave, visit Bear Den for outstanding croissants and brunch options, and of course….coffee.

As your visit here draws to a close, we hope you will have enjoyed every adventure and marveled at all that the town has to offer. Depart with unforgettable memories and experiences, and plan another adventure here again in the future!


Aspen is the ideal destination for a vacation any time of year, but ski season is where Aspen truly shines. With four mountains for all levels of skiing plus a fantastic après scene, you can’t beat an Aspen winter vacation.
At Aspen Square, we offer the convenience of walking to the mountains, hiking trails, downtown restaurants, shopping, and special events. We are located just a block from the main free skier bus terminal, which will take you to Buttermilk, Snowmass, or Aspen Highlands, with the Aspen Mountain gondola only one block away.
Explore our Aspen condo rentals to view our available rentals and start planning your ski vacation. Call (970) 925-1000 and let us help you get your vacation started, or contact Aspen Square’s Reservations desk ( for assistance booking your stay with us.