The Best Winter Week in Aspen: Your Ultimate Itinerary
Winter in Aspen feels like stepping inside a snow globe — twinkle lights, fresh powder, cozy fireplaces, and some of the best skiing and dining in the world. Whether you’re here for the slopes, the après scene, or a little luxury mixed with adventure, this itinerary delivers the perfect winter week in Aspen.
Day 1: Arrive + Explore the Winter Glow of Downtown
Ease into your trip with a walk through Aspen’s winter-lit core. Grab a latte or hot chocolate from Paradise Bakery and wander the pedestrian malls lined with holiday lights and snow-dusted storefronts.
Where to Shop
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Little Bird or Susie’s for luxury consignment
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Kemo Sabe for iconic cowboy hats and western flair
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Carl’s Pharmacy, an old-school Aspen staple for general store necessities and cosmetics
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Pitkin County Dry Goods for winter style
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Frame, Revolve, Citizens of Humanity, Rag & Bone, and Ralph Lauren for fashionable everyday wear
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Gucci, Prada, Louis Vuitton, Dior, Loro Piana, and Brunello Cucinelli for exquisite luxury brands
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Performance Ski, Aether, Gorsuch, and Fusalp for elevated ski looks
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O2 Aspen for knits, curated home pieces, and beauty
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Staud Pop-Up at the St. Regis (seasonal)
Dinner: Start with Clark’s Oyster Bar — the chowder and martinis hit especially well on a cold night.
Nightcap: J-Bar, The Living Room, or Bad Harriet at Hotel Jerome for a true Aspen classic.
Day 2: First Ski Day on Aspen Mountain + Iconic Après
Kick off your ski trip on Aspen Mountain. Start with groomers off the Silver Queen Gondola and ease into steeper terrain as the day goes on.
Late Breakfast: Grab the famous pancakes at Bonnie’s before 10:30 a.m.
Après: Head straight to Ajax Tavern for truffle fries, rosé, and unbeatable people-watching.
Dinner: Matsuhisa for sushi, cocktails, and an intimate winter atmosphere.
Evening: Check the lineup at Belly Up or head upstairs to AM7 for elevated nightlife.
Day 3: Snowmass Ski Day + Sunset Cocktails
Spend the day exploring Snowmass Mountain with expansive terrain and options for all levels.
Lunch: High Alpine or Toro at the Viceroy.
Après: Venga Venga, Viewline Hotel Bar, or swing back to Aspen for Snow Lodge’s DJ sets and lively après scene.
Dinner: Ellina for Italian comfort food and a warm, buzzing atmosphere. Don’t miss the artichoke bruschetta with parmesan fondue and shaved black truffle.
Day 4: Adventure Day
A winter trip to Aspen isn’t complete without an off-the-grid adventure.
Choose One
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Snowmobile to the Maroon Bells or backcountry with Western Adventures or T-Lazy-7
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Cross-country skiing at the Aspen Nordic Center
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Ice skating at CP Burger’s outdoor rink
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Skin up Tiehack for sunrise breakfast on Friday mornings
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Winter hike up Smuggler, a local favorite year-round
Lunch: French Alpine Bistro — the most romantic spot in Aspen.
Dinner: Steakhouse No. 316 — rich, moody, and perfect after a big day outside.
Day 5: Spa, Shopping & a Slower Day
Recharge with a relaxing morning.
Spa Picks
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Remède Spa at the St. Regis
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The Little Nell Spa
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O2 Aspen for facials and massage
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Aspen Luxe Med Spa for nails, facials, and skin treatments
Spend the afternoon browsing Aspen’s boutiques, galleries, and seasonal pop-ups.
Lunch: Las Montañas — fun, buzzy, and the fajitas never miss. Stay for happy hour from 3–5 p.m.
Dinner: Take a horse-drawn sleigh to Pine Creek Cookhouse, a legendary alpine restaurant tucked at the base of the Elk Mountains. Wild game, fresh fish, and locally sourced ingredients make this one of Aspen’s most magical winter dining experiences.
Day 6: Highlands + Cloud Nine Magic
No Aspen winter itinerary is complete without Aspen Highlands.
Morning: Ski Highlands Bowl if conditions (and your legs) allow.
Lunch & Après: Cloud Nine Alpine Bistro for European-style après, fondue, champagne spraying, and Pyramid Peak views. Book well in advance.
Pro Tip: For groups of 30–45, book the cat ride up for a private evening seating — one of Aspen’s most unforgettable dining experiences.
Dinner: Keep it casual with Wild Fig, always reliable and delicious.
Day 7: Slow Morning + Farewell Dinner
Savor your final morning.
Brunch Options
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Bear Den
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Prospect at Hotel Jerome
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Poppycocks
Spend your last afternoon wandering snowy sidewalks, finishing up shopping, or squeezing in one more run on Ajax.
Final Dinner: Celebrate the end of the trip at Cache Cache, Parc Aspen, or Casa Tua — three Aspen favorites.
Final Tips for the Best Winter Week in Aspen
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Book early: Holiday dining, Cloud Nine, and activities fill quickly.
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Pack layers: Aspen temperatures change fast — bring base layers, warm boots, and a good coat.
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Walk everywhere: The downtown core is incredibly winter-friendly.
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Don’t skip après: It’s truly part of the Aspen experience.
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Catch a show: Belly Up, AM7, Snow Lodge après, and Viewline concerts always bring energy to town.
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Tour property while you’re here: If Aspen is on your radar, winter is the perfect time to see homes in person.
Aspen is always a good idea.
