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Concierge.com's insider take:
The Aspen ski season starts in late November and runs through mid-April. There are four mountains here: Aspen Mountain (a.k.a. Ajax), Aspen Highlands, Buttermilk, and the enormous, aptly named Snowmass (home to the longest and highest lift-served vertical rise in the country). Combined, they comprise 341 trails (316 miles covering 5,246 acres) served by 45 lifts capable of hauling more than 50,000 snow warriors an hour.
Thanks to 3,128 acres of varied terrain, skiers of all levels do well on Snowmass, earning its reputation as one of the best family resorts anywhere. And with a new learning area and lift at the top of the gondola, three new magic carpets, and the $17-million Treehouse Kids' Adventure Center—complete with Disneyland-like bear caves, beaver dens, and trout ponds—your little cubs will definitely agree. But the hill's friendly vibe shouldn't deter the double-diamond set: The Cirque Headwall serves up honest steeps that put your heart squarely in your throat. Visitors do have one gripe about the place: the lack of a base village, which is currently being solved by a massive development project. (The mountain is six miles outside of town.)
The other three mountains are all within a three-mile radius of downtown. Buttermilk, the site of ESPN's Winter X Games, is also a good choice for the novice—15 of its 42 trails are deemed easiest. Also a good bet for avoiding crowds. Aspen Mountain rises straight up from downtown, and is suited for experts (there are no bunny slopes). There is the classic World Cup–cruiser Ruthie's Run, and thrilling steeps like S1. There are also more famous and eccentric people than you'll be able to shake your pole at.
Aspen Highlands is where the locals play, and is generally the least crowded, with an average of two people per acre. It's also home to the hike-to Highlands Bowl, some of the steepest and deepest in-bounds terrain in Colorado. The hike—a 45–60 minute slog up a bootpack—is best for diehard experts, and those turns that are definitely worth earning. If that's not for you, don't worry: Deep Temerity's steep, moguled chutes will lend bragging rights, too. For the blue-square set, the long, rolling cruisers off the Cloud Nine chair are some of the best around.