Winter in Aspen is at its best when everything feels effortless. Staying in downtown Aspen allows you to enjoy skiing, dining, culture, and evenings out without worrying about winter driving conditions or coordinating transportation. With the mountain, restaurants, shops, and entertainment all within walking distance, you can experience Aspen fully, even on a short weekend.

Here’s how to spend a perfect winter weekend in Aspen without a car.

Friday Evening: Arrive, Settle In, and Head to Dinner

After arriving in Aspen, take a short walk into town and ease into the weekend. Downtown Aspen comes alive in the evenings during ski season, with restaurants and music venues clustered within a few walkable blocks.

For dinner, head to Campo de Fiori, a longtime local favorite known for its relaxed, unpretentious atmosphere and consistently good Italian food.

📍 205 S Mill St, Aspen, CO 81611
🔗https://www.campodefiori.net/

If you’re in the mood for something more elevated, Betula offers refined, ingredient-driven cuisine with French and European influences, an intimate dining room, and a thoughtfully curated wine program.
📍 303 E Main St, Aspen, CO 81611
🔗https://www.betulaaspen.com/

Saturday Morning: Ski Ajax or Ride the Gondola for the Views

Start your day at Ajax Mountain, located just steps from downtown Aspen. Skiers can spend the morning on Ajax’s groomers and steeps, while non-skiers or mixed groups can ride the gondola to the top for sweeping views of the Elk Mountain range and the surrounding peaks.

Before or after heading to the mountain, grab coffee and a bite at Sant Ambroeus, a downtown staple for espresso, pastries, and light breakfast fare.
📍 520 E Hyman Ave, Aspen, CO 81611
🔗https://www.santambroeus.com/pages/aspen

Saturday Lunch: A West Aspen Walk or Downtown Favorites

From downtown, take a scenic walk toward Aspen’s West End, known for its beautifully preserved historic homes. If you’re up for the stroll, Hickory House is located in West Aspen and is a true Aspen institution, famous for its no-frills setting and generously portioned ribs — a favorite of locals and visitors alike. Even Gigi Hadid has said they’re her favorite ribs, sharing the spot on Instagram.
📍 730 W Main St, Aspen, CO 81611
🔗https://www.hickoryhouseaspen.com/

If you’d prefer to stay closer to the center of town, downtown Aspen offers several excellent lunch options, all within easy walking distance:

• White House Tavern
  A lively downtown favorite with a social, energetic vibe, known for classic comfort food and an atmosphere that’s as much about people-watching as the menu.
  📍 302 E Hopkins Ave, Aspen, CO 81611
  🔗https://www.whouseavern.com/

• Clark’s Oyster Bar
  Polished yet approachable, Clark’s is a reliable go-to for oysters, seafood, and classic dishes in a comfortable downtown setting.
  📍 110 E Main St, Aspen, CO 81611
  🔗https://www.clarksoysterbar.com/

• Meat & Cheese
  Casual and unfussy, Meat & Cheese is ideal for an easy midday meal, offering sandwiches, salads, and market-style fare perfect between skiing and shopping.
  📍 308 E Hopkins Ave, Aspen, CO 81611
  🔗https://www.meatandcheeseaspen.com/

Saturday Afternoon: Ice Skating, Spa Time, or Yoga

Spend the afternoon ice skating at Silver Circle Ice Rink, located right in the heart of town.
📍 425 Rio Grande Pl, Aspen, CO 81611
🔗https://www.aspenrecreation.com/parks/silver-circle-ice-rink

For relaxation, book a spa treatment at The St. Regis Aspen Resort, known for its full-service spa and wellness offerings.

📍 315 E Dean St, Aspen, CO 81611
🔗https://www.marriott.com/en-us/hotels/aspxr-the-st-regis-aspen-resort/overview/

Or drop into a yoga class at O2 Aspen, a longtime local studio offering a variety of classes.
📍 501 Rio Grande Pl #102, Aspen, CO 81611
🔗https://www.o2aspen.com/

Saturday Night: Music, Theater, and Winter Evenings

After dinner, catch a live show at Belly Up Aspen, one of Aspen’s most popular venues for touring musicians and DJs.
📍 450 S Galena St, Aspen, CO 81611
🔗https://bellyupaspen.com/

You can also check the schedule at the Wheeler Opera House, a historic downtown venue that hosts concerts, performances, and speaker events throughout the winter.
📍 320 E Hyman Ave, Aspen, CO 81611
🔗https://wheeleroperahouse.com/

Why Staying Downtown Makes Winter Easy

In winter, staying downtown allows you to enjoy skiing, dining, and nights out without worrying about snowy roads or late-night transportation. Being able to walk from the mountain to après-ski, dinner, or a show, and then return home comfortably, makes the experience far more relaxed and flexible.

Hotels like The Residence Hotel Aspen, located just steps from Ajax Mountain, offer the advantage of downtown access paired with suite-style accommodations. With space to unwind and select suites offering kitchens or kitchenettes, it’s an ideal home base for winter weekends or longer stays that feel effortless and connected to town.

And for guests who want more space, a longer stay, or a deeper connection to Aspen, Susan Stone-Chen and SSC & Company can assist with finding larger downtown rentals or exploring what a permanent home in Aspen could look like. Whether you’re extending your stay or considering putting down roots, having local expertise makes the transition seamless.