When it comes to winter, out west is best. And there’s no more glamorous spot for early-season tracks than Aspen, Colorado. The land of chic cowboy hats and expensive boots and turquoise accessories galore, Aspen is appealing to travelers on and off the slopes thanks to its bustling nightlife scene and thriving art galleries and boutiques. But for true winter adventurers, Aspen Snowmass is unrivalled for its four distinct mountains—Buttermilk is best for beginners, Snowmass has something for everyone, Highlands is beloved for its Cloud Nine champagne-spraying, and Ajax (the town mountain) offers long, gorgeous vertical runs and a base that’s right in the heart of town.
Aspen’s storied history is filled with unrivalled hedonistic bacchanalia—with Hunter S. Thompson as its patron saint—and modern-day Hollywood glamour (courtesy of beloved residents Goldie Hawn and Kurt Russell, of course). But, you needn’t be a celebrity to feel like one during your winter trip to Aspen this season. From gorgeous, open trails (a benefit to skiing in a town where skiing isn’t the only priority means less crowded lift lines) to an array of apres options (which don’t require prior downhill exercise as a point of entry) to ultra-luxurious accommodations, there’s something for everyone in Aspen. Winter is coming, here’s your guide for how best to enjoy it in this magical town within the Rocky Mountains.
Eat
(Photo provided by Katherine Parker-Magyar)
Pine Creek Cookhouse, 11399 Castle Creek Rd, Aspen, CO 81611: This Aspen institution is quite literally off the beaten path. Located at the base of the Elk Mountains, with stunning views of the Ashcroft Valley, visitors can opt to cross-country ski to their reservation and soak up the views. (Pine Creek Cookhouse is also accessible via car, of course, but why not get into the spirit of the season?). From there, the world is your oyster: sleigh riding, snowshoeing, gourmet meals. What's not to love?
Cache Cache, 205 S Mill St, Aspen, CO 81611: Cache Cache is a wonderful date night option in Aspen—French is a Romance language for a reason. The vibe is cozy-chic, and the cuisine is upscale, with a certain cache if you will forgive the pun. We suggest the Colorado Rack of Lamb and the Escargots à La Bourguignonne.
Kenichi, 533 E Hopkins Ave #2, Aspen, CO 81611: Another popular date spot in Aspen, Kenichi is known for its intimate atmosphere and upscale, trendy decor. And, the world-class sushi, of course. (This is Aspen. Duh.). Order the Misco Black Cod and the Dynamite Shrimp—best paired with a Sake-Tini (cucumber vodka, Midori, lemon and nigori sake).
Campo de Fiori, 205 S Mill St, Aspen, CO 81611: A constant classic, Camp de Fiori delivers on delicious Italian food right in the heart of town. Head here after an apres well-spent, or make this the last spot of the night—it’s a perfect nightcap option before turning in for the evening. Of course, like many Aspen establishments, Campo de Fiori does get quite crowded during peak season, so a reservation is recommended, especially for dinner.
Cloud Nine, Boomerang Rd, Top of the Cloud Nine Lift, Aspen, CO 81611: This Alpine bistro is home to the rowdy, champagne-spraying parties you see all over social media, from opening weekend all the way through early spring. Located on Aspen Highlands, we suggest making a reservation in advance, and being realistic about your level of ski abilities when it comes to navigating the downhill afterwards. What goes up, must come down, and nothing is worse than a torn ACL (speaking from experience).
Drink
(Photo provided by Katherine Parker-Magyar)
Woody Creek Tavern, 2858 Upper River Rd, Woody Creek, CO: Woody Creek Tavern is a must-visit spot in Aspen, in any season. Bike to Woody Creek Tavern when the weather's a bit warmer to check out Hunter S. Thompson's favorite bar in Colorado. It doesn't disappoint. In the warmer months, head there on #TuesdayCruiseDay: meet up with fellow cycling aficionados at Aspen Brewing Co. before setting off on your trail. In the winter, opt for a cross-country ski trip.
Caribou Club, 411 E Hopkins Ave, Aspen, CO 81611: The Caribou Club is the first members-only club to grace Aspen, established in 1990. If you're wondering why it took the posh resort town so long to introduce private clubs, you're not the only one. The vibe is infectious upon entering, however, so do try to pull some strings.
Escobar, 426 E Hyman Ave, Aspen, CO 81611: This Pablo-themed nightclub really sets the bar high on their website: "Descending into the sleek underworld of Escobar, guests should get ready to transform into their boldest, sexiest selves." Trust us when we say, it delivers.
Zane's Tavern, 308 S. Hunter St. Aspen, CO 81611: This bar's slogan proudly proclaims to be "Where the Locals Go". And, according to the locals, it's true. But, it’s also a great time for weekend visitors—more low-key than other spots, with a cozy and casual vibe.
Stay
(Photo provided by Katherine Parker-Magyar)
The Gant Aspen, 610 S W End St, Aspen, CO 81611: If you want to feel like you own a glorious cabin in Aspen without the hassle of maintaining it (or the millions of dollars required to actually purchase one), then book a stay at The Gant Aspen. The wonderfully spacious accommodations are perfect for some R&R after the slopes, and the convenient location is perfect for walking to and from town at ease—though the hotel also provides on-demand in-town and airport shuttles from 7am to 11pm daily, in case you’ve gotten enough exercise on the slopes already.
Aspen Meadows Resort, 845 Meadows Road, Aspen, CO: If you’re looking for the best of both worlds—a country escape within easy walking distance to downtown—then look no further than Aspen Meadows Resort. The suite-style accommodations are perfectly suited to groups, and the expansive property is home to an array of culturally immersive experiences, including three art galleries and striking outdoor sculptures. The heated pools and hot tubs are magnificent, and the tennis courts are perfect for guests visiting in warmer months—Aspen has as much to offer in the summertime as in the winter, of course.
Limelight Snowmass, 65 Wood Rd, Snowmass Village, CO 81615: Snowmass is truly the best mountain for skiers looking to maximize their time outdoors, with an array of trails for all levels of athlete. And Limelight Snowmass is perfectly suited to winter adventurers, ideally located at the base of the Elk Camp Gondola. Perfect for ski-in, ski-out access and an easy walk to all the shops and restaurants in the heart of Snowmass village.
Hotel Jerome, 330 E Main St, Aspen, CO 81611: If you want to stay at a true Aspen icon, then look no further than the Hotel Jerome. And, even if you don’t end up booking a room, this spot is a must-visit for cocktails and dinner, as well—we recommend the Living Room or the J-Bar as all-season hangouts to see and be seen.
The St. Regis Aspen, 315 E Dean St, Aspen, CO 81611: Another can’t-miss spot in Aspen. In a town defined by luxury, the St. Regis Aspen takes matters to a whole new level, with butler service and daily champagne sabering. Enjoy the full-service spa and outdoor pool at your fingertips, but if you do feel like exploring the surrounding town, Aspen’s many shops and restaurants are within walking distance.
Explore
(Photo provided by Katherine Parker-Magyar)
Hit the Slopes in Snowmass, Snowmass Village, CO 81615: Enjoy the gorgeous views of the valley and wide-open trails at Snowmass, which is popular with skiers of all levels due to its varied terrain. The resort boasts the highest vertical rise in the country, and experts will be sated by the side-country and pipe skiing options, while the expansive groomers are perfect for families of mixed abilities to enjoy a day outdoors. The easiest mountain, of course, is Buttermilk, which—though it doesn’t quite offer the same vertical drop—does deliver on gorgeous views. (This is Aspen, after all.)
Hike Highlands Bowl, Aspen Highlands: A beloved pastime by mountain adventurers, hiking Highlands Bowl is a gorgeous way to spend an early morning or afternoon (though we suggest setting out first thing, to get the hard part out of the way). Reward yourself with some champagne and fondue at Cloud Nine later on.
Ski Hut Trips, Aspen Snowmass: Rent a backcountry hut and prepare to really venture into the wild (outhouses required). These trips are a true paradise found for skiers and snowboarders, and each itinerary can be selected to suit varying levels of experience, particularly in regards to the remoteness of the trails and difficulty of terrain.
Snowmobile to Maroon Bells, Maroon Bells–Snowmass Wilderness: Get ready for your most-liked Instagram post ever: the 14,000-foot Maroon Bells are the two most photographed peaks in North America, and it’s impossible to take a bad picture. But do make time to put your phone away and take a snowmobile tour to explore the glacial valley.
Pitkin County Dry Goods, 520 E Cooper Ave, Aspen, CO 81611: The spot to visit for all of your swag: "Aspens Original Clothing Store." Head home looking a little bit sharper than you did when you left.
Kemo Sabe, 217 S Galena St, Aspen, CO 81611: Lastly, did you really visit Aspen without paying a visit to Kemo Sabe and setting a hat (and your wallet) on fire in pursuit of some high-end country swag? While the classic hats are a true investment, shoppers can also find an array of turquoise jewelry and high-end accessories, too. And it’s the perfect apres activity—invest in some accessories for a night out on the town, the perfect setting to show off your wares. In Aspen, being all hat no cattle isn’t necessarily a mark of shame (but, trust us, don’t try this in Jackson.)
