Aspen Winter Wonderland: 4-Day Ski-In, Ski-Out Adventure Itinerary

Fuel up for the day with breakfast at Aspen Hickory House, famous for its barbecue. Then, catch the first gondola up to Aspen Mountain (Ajax) for early morning skiing. Enjoy the fresh powder and the stunning views of the surrounding peaks.

Take a break from skiing and have lunch at Ajax Tavern right at the base of the mountain. Afterward, continue your skiing adventure or if you prefer, explore the Aspen Scavenger Hunt which will take you to hidden gems around the town.

Dine at Plato's Restaurant, located at the Aspen Meadows Resort. The restaurant offers a sophisticated, yet relaxed atmosphere with panoramic views of the Aspen Highlands. After dinner, unwind with a drink at Zane's Tavern Aspen, a local favorite with a laid-back vibe.

Take a day trip to the nearby Snowmass area. Enjoy breakfast at Bear Den Aspen before hitting the slopes at Snowmass Mountain, known for its wide range of terrain. Spend the morning skiing or snowboarding in this expansive ski area.

For lunch, head to Aspen Public House in downtown Aspen. Afterward, return to Snowmass and experience the Ullr Nights - Snowmass Mountain (if available). This unique event offers snowshoeing, tubing, and live music in the evening.

After a day of skiing and activities, relax with a comforting dinner at White House Tavern. Then, enjoy the vibrant après-ski scene at Pussyfoot Steeps, a bar known for its lively atmosphere and signature cocktails.

Begin with breakfast at Silverpeak Grill, a local favorite. Then, take a guided Aspen Dark History Ghost-Themed Guided Walking Tour to uncover the mysterious and eerie tales of Aspen's past. It's a unique way to start your final day in the mountains.

For lunch, visit Clark's Oyster Bar - Aspen for a taste of the sea in the heart of the Rockies. Post-lunch, explore the Aspen Art Museum to appreciate contemporary art and the stunning architecture of the museum building.

Conclude your Aspen journey with a memorable dinner at Jing Aspen, offering a blend of Chinese and Japanese cuisine in a stylish setting. After dinner, if time allows, take a scenic drive to the Maroon Bells or simply enjoy the serene mountain views from downtown.