A Winter Weekend in Aspen

Aspen, Highlands and Buttermilk at Dusk Panorama

Day 1:

A Winter Weekend


Before you hit the slopes for your winter weekend in Aspen, you’ll need to set your bags down and possibly nap off your flight. May we suggest the Alm Haus? It’s the perfect home in the middle of the town to fit any weekend getaway in Aspen. The Colorado Cabin décor will get you in the mood to hit the slopes ASAP. For a bigger group, try Mountain Valley Retreat or Silver Kingdom!


Aspen offers four mountains for skiing, which are all a part of White River National Forest, the largest forest in Colorado. Buttermilk, Aspen and Highlands are in Aspen proper, while the adjacent Snowmass, just a short drive from town, boasts as many lifts as the other three combined.


More advanced skiers flock toward Aspen Mountain, rising up from the center of downtown. All the locals can be found at Highlands with its expert terrain and the attraction of the Highlands Bowl. Buttermilk and Snowmass both boast premier terrain parks. Choosing any of the four will not disappoint – just have your ability in mind upon making the tough decision.


For any non-skiers, there are sightseeing passes for the mountains that can get you to the top of the mountain for some great Instagrams. Or hit the town! Shop to your hearts content in the downtown core or hit a yoga class at O2 Aspen.


Ajax Tavern is the perfect place for groups to meet for lunch. Located right next to the Silver Queen Gondola, it is known both for its views of the Aspen Mountain slopes and its incredible food, which includes a raw bar, fondue and one of the juiciest grass-fed burgers in town. Yum!


If you manage not to eat yourself into a food coma, opt for a snowshoeing tour of Aspen Mountain, led twice daily by naturalists from the Aspen Center for Environmental Studies. Or, for a faster change of pace, T-Lazy-7 Ranch spearheads exciting snowmobiling adventures through magnificent Aspen groves ending at the base of the breathtaking Maroon Bells — while still somehow getting you back to town in time for après-ski.


An après hot spot for locals and tourists alike is 39 Degrees at the Sky hotel right at the base of Aspen Mountain. Or if you’re in Snowmass, try Venga Venga or Zane’s Tavern for some drinks to numb the wobbly legs. Afterwards, head to any of the restaurants downtown for some fabulous food to soak up your après skiing cocktails. Later, enjoy the Aspen nightlife, or retire full, happy, and tired to prepare for your next day!


Day 2:

A Winter Weekend


Get the day going and stock up on some much needed energy for a second day of hitting the slopes at Main Street Bakery. It’s one of the best breakfasts in town and just blocks from the Alm Haus in downtown Aspen; corn beef hash is our go-to, and it’s certainly not from the can!


If you didn’t hit the slopes yesterday, try Buttermilk today. It is a versatile mountain and some even say it’s the best in the world for beginners to find their footing. There are certainly challenging trails as well as the beginner terrain making it great for a whole group of varying abilities. Additionally, The Hideout, a newly redesigned children’s center operated by the ski school at the base of the mountain, gives parents a breather while kids enjoy imaginative, nature-focused programming. Check out lessons, rentals, and lift tickets here.


When it’s time for dinner, make your way to the newly opened Meat & Cheese, a place already garnering attention for its upscale farmhouse cuisine and to-go market pedaling cured meats, cheeses and handcrafted pantry items. Its menu ranges from boards highlighting rotisserie chicken or porchetta to globally influenced dishes, like rice dumplings with shredded pork and Korean chili sauce, and lamb korma with scallion pancakes, chai-pickled grapes, yogurt and mint.


Where better to head with a full belly than Belly Up? Aspen’s premier music venue has hosted musical legends like B.B. King, Snoop Dogg, Lynyrd Skynyrd and many more. The lineup is always top notch, and the intimate venue is something everyone enjoys experiencing. Or, try the historic Wheeler Opera House for some nighttime entertainment.



If you’d rather ditch the bar line for bottle service, David Arquette’s club Bootsy Bellows might be more your style. Much like the original West Hollywood location, the Art Deco lair showcases lush couches, dark corners, burlesque performances, dancing puppets and magnum bottles of just about anything your heart desires. After all, you are in Aspen.