Aspen is one of the world’s most famous ski destinations—and one of the most confusing for first-time visitors. Aspen is an attitude and an atmosphere, but also a town, region and one of several ski resorts, so it helps to know just which Aspen you want.
The town of Aspen, like many ski towns in the American West, started out as a mining camp before switching to the pursuit of winter’s white gold, and silver was the element that put it on the map. But while silver is fairly pedestrian as precious metals go, Aspen is anything but, and along the way was transformed into a destination popular with the rich and famous, not as overtly fancy as Deer Valley or Beaver Creek, but tonier than either, and the most urban of its peer group.
Even the grid layout of town bears a passing resemblance to midtown Manhattan, versus the Old West style Main Street with wooden sidewalks found from Telluride to Breckenridge to Park City. Yet, despite its penchant for designer ski suits, furs and chic European eateries, Aspen has a surprisingly rugged side and extremely active year-round population, offering skiing and snowboarding terrain more extreme and extensive than at its highbrow siblings. In short, it can be almost all things to all people if you know where to look—and where to stay.
Mountains & Towns
When most people say they are going to Aspen on a ski trip, they mean the greater Aspen area, or Aspen Snowmass, rather than the town. The family-owned Aspen Skiing Company is comprised of four very distinct mountains spread out over a 10-mile stretch, and Snowmass, the largest of these—by far—is also the furthest from the namesake town. So the first step is deciding where to stay, and this is based largely on your ability, the composition of your group, and whether your priority is skiing or everything else – shopping, nightlife, dining, and energy.
Snowmass is the only mountain here that would be a true destination ski resort on its own and is one of the nation’s largest with nearly 100 trails across more than 3,300 skiable acres served by 21 lifts. Nicknamed “Snowmassive,” it is appreciably bigger than its three sister mountains combined, the only one that offers a true “big mountain” experience. It skews more challenging, with only 6% of its terrain green, and the rest evenly split between intermediate and more difficult to expert. Nonetheless, what beginner terrain it does have is superlative, in a mid-mountain area around Elk Camp that is higher than most beginner offerings elsewhere, with panoramic big mountain views and confidence-boosting separation from overzealous skiers, plus the quality of the ski school makes it a great place to learn.
Intermediates have vast offerings to explore, and in general, it is one of the least crowded mountains, with low skier per acre density. Experts love the easy access to the kind of terrain that normally requires hiking or side country gates. The Hanging Valley area has the region’s steepest runs, a rugged bowl, the Cirque, and all the double-black cornices, chutes, cliffs, and glades you could want. Snowboarders also love the layout at Snowmass, and finally, it has excellent and multiple terrain parks and a huge superpipe.
Snowmass is a near perfect ski resort, its only drawback being its location, just far enough from the town of Aspen to be inconvenient for more than maybe a single dinner night out or day trip during a ski week. Snowmass village has grown in recent years, shaking its “Slowmass” image with new hotels and restaurants, but it still not a town, and is best for family gatherings and escapism. In this vein, it features skiing’s finest dedicated, supervised children’s facility, the three-story, 25,000 square foot Treehouse. Houses here are larger, less expensive and almost all are ski-in/out (which doesn’t exist in Aspen). Snowmass is the top choice for those who want lots of skiing and lots of relaxation or family time while catering to all abilities.
Aspen itself is far more cosmopolitan and action-packed, ideal for couples and groups without kids who want to do more off the slopes and out of the house. But the marquee in-town mountain Ajax, more commonly called Aspen Mountain, is by far the smallest of the group and tiny by national standards at under 700 skiable acres. Some first timers arriving in Aspen to all the hype are underwhelmed by its namesake peak, but it skis much bigger than it looks, with a lot of vertical rise and steep, challenging terrain. In fact, this is the bigger surprise to many newcomers—this is the only major resort in the country with no beginner skiing, zero green terrain, a shock to the less skilled or those with kids.
The good news is that so many people staying in town don’t like to ski ungroomed terrain that it is awesome on powder days. Aspen Mountain is for intermediates and above, but that does not mean those learning to ski must forego town; staying here also gets you much easier access to the other two mountains, Aspen Highlands, and Buttermilk. Both are three miles away with very easy and user-friendly free shuttle buses (which also serve Snowmass). Both are day areas, with some food and shopping but no lodging or villages.
Buttermilk is designed for learning, a mainly beginner and intermediate mountain that is one of the finest places in the entire country to learn how to ski or snowboard, and the reason many people choose it. Conversely, Aspen Highlands is the locals’ favorite and known for its expert terrain, and the relatively short (under 30 minutes) hike to ski famed Highlands Bowl is a rite of passage for Aspen visitors. But like Aspen Mountain, Highlands has no green terrain and less than a quarter is intermediate, with 67% devoted to black and double black, including extensive new glade areas. For advanced skiers, it is fantastic, with more than 100 trails packed into just over 1,000-skiable acres, for lots of skiing and little wasted time.
Lodging: Staying in Snowmass is turnkey, one mountain, all abilities, ski-in/out. An Aspen town stay offers more variety and puts all sorts of non-skiing attractions at your doorstep, but usually means splitting between multiple mountains on different days, even for experts, and potentially splitting up groups or families among the three mountains. The payoff is all the town offers—which is a lot.
Shopping, Dining and More
Shopping & Activities: This is all in the town of Aspen, which has more boutiques (Prada, Bogner, Moncler, etc.) than any other North American ski town, as well as outdoor gear, Western wear, and more. Just walk the downtown core and Hyman Street pedestrian mall and you can’t miss it. There are also plenty of local adventures and outfitters, from cross country and guided backcountry skiing (try the well-regarded Aspen Expeditions) to hot air ballooning, winter fly fishin, and snowmobile tours.
Dining & Drinking: In Snowmass, options are high quality but limited. For fine dining the top pick is TORO Kitchen & Lounge in the Viceroy. Celebrity chef Richard Sandoval’s menu fuses Pan-Latin American dishes with locally sourced Colorado organic and grass-fed products, plus offers a great craft cocktail and barrel-aged spirits program. Sage, in the Snowmass Club has similar sourcing but with a more traditional upscale Rocky Mountain menu featuring elk, trout and duck. If you have kids in tow, don’t overlook Slopeside Lanes, with bowling alleys featuring cushy leather couches, lots of flat screens and arguably the best pizza in Snowmass, plus wings, sliders and burgers. New this winter is Francesca’s Empanadas, a grab and go spot open from morning to night with Argentinean pastas and empanadas. Family friendly Mountain Bayou offers an eclectic mix of traditional Southern and Cajun/Creole dishes.
Beginner-centric Buttermilk has the least interesting offerings and skews more cafeteria style, but for this winter got a surprisingly good and authentic Southern barbecue spot, Home Team BBQ, right at the base. Aspen Highlands has just two on-mountain options, the main Merry Go Round cafeteria with vast outdoor seating, and the world-famous Cloud Nine. This European Alps-inspired chalet does raclette and fondue for lunch and then turns into one of the most raucous and glitzy après spots in American skiing, complete with champagne spraying and dancing on the tables. Ski patrol forces everyone out shortly after the lifts close, but from 2PM until then, this is the prime Ibiza-style party spot in Colorado. If you want lunch, make a reservation (12 for eating or 2 for the crazy scene). Cloud Nine is also open sporadically for quieter sno-cat dinners.
In Aspen you will be spoiled for choice. For après drinks, the traditional power spot is the bar in the slopeside Little Nell Hotel, but competition has surged in recent years. 39 Degrees in the Sky Hotel has a contemporary day club feel with couches, complicated signature cocktails, and low lighting. The bar in the revamped Hotel Jerome has an upscale Old West aesthetic, but the hotel also does more rarefied cocktail service in its gorgeous lobby. The Limelight hotel lobby bar is the Millennials’ choice, with group tables, craft beer and happy hour gourmet flatbreads from the brick oven, a more social flair. The classic ski bum vibe is alive and well at Aspen’s oldest saloon, the Red Onion, with live music often, the newest urban addition to the scene is Brooklyn-style hidden downstairs speakeasy, Hooch.
Fine Dining: Fine dining choices also boggle the mind. Tops in town is generally considered Element 47 (silver!) in the Little Nell, with its award-winning wine list and impeccable ingredient sourcing. With no dress code, it has gone more casual in recent years, but the food is still great. There is a lot of upscale Italian here, but for over a decade, L’Hostaria has wowed with specialties of Northern Italy (risotto, veal Milanese, carpaccio), a chef/owner out of two and three-starred Michelin kitchens in Italy, and a great wine list packed with Super Tuscans.
Sushi fans justifiably adore Matsuhisa, a sister to legendary chef Nobu Matsuhisa’s LA flagship. Besides amazing sushi and fish flown in daily from around the world, there are Nobu’s signature dishes, miso-glazed black cod, and rock shrimp tempura. The formal dining experience is downstairs, but there is a pub-like casual lounge, beloved by locals, hidden upstairs with flat-screen TVs and more casual menu items.
Kenichi is another great high-end sushi spot, an offshoot of a famed Austin sibling. Cache Cache is a tony longtime favorite for precious French-American cuisine such as beef tartare using locally produced, natural Wagyu-influenced 7X beef, some of the best in the United States. If you have kids in tow, consider a night out at the Pine Creek Cookhouse. You arrive at this ranch-style Old West spot and longtime Aspen favorite by horse-drawn-sleigh or under your own power on cross-country skis, for an offbeat mix of classic Colorado dishes (trout, lamb, elk chops) and Nepalese specialties, such as bison momos (traditional Nepalese dumplings). The four-course dinner menu has lots of choices, ending with decadent desserts (pretzel bread pudding, apple crisp) and there is also a more traditional children’s menu (mac & cheese, burgers). It is also open for lunch, with cross-country ski rentals and more than 20 miles of groomed Nordic trails.