Overall Rank: #7
Aspen is the original American ski town, and it holds attractions far more diverse than just groomed and ungroomed snow. Everyone focuses on the money and glitz of Aspen, which are an undeniable part of its personality-celebrity spotting is a minor sport-but the town is much more multidimensional. There are posses of hardcore telemarkers, countless talented racers, and a great backcountry culture. The food is epic, the bars are world class, and there's a killer little bookstore right on the main drag.
There is, of course, skiing, too. Though both Aspen and Highlands are on the small side (10 Aspens would fit into Whistler Blackcomb), there's white-knuckle terrain to be found. Local skiers have always gravitated to Highlands, which has more vertical and acreage and boasts purer fall lines. The choicest areas are the ultrasteep shots through the trees off east-facing Steeplechase Bowl and northwest-facing Olympic Bowl. And with the opening of avy-prone Highland Bowl (it was off-limits for years), you can take your pick from a vast swath of 40- to 45-degree lines. Aspen Mountain isn't exactly pancake-flat, either, though it has a few too many off-camber pitches for some. But locals know you can milk the double fall lines by zig-zagging your way across the face. And after a storm, Bell Mountain is your best bet for sustained powder turns.
Top Elevation: Aspen, 11,212 feet; Highlands, 11,800 feet.
Vertical: Aspen, 3,267 feet; Highlands, 3,635 feet.
Snowfall: Aspen, 251 inches (11,190');Highlands, 239 inches (11,100')
Acres: Aspen, 673; Highlands, 790
On Highlands, if conditions are good (and so are you), head for Highland Bowl. You'll get a good exchange rate on the hump up to White Kitchen; the payoff is a long pitch with an average of 38 degrees and a potential for air at the bottom.
Though Aspen gets a modest 250 inches a year and almost a quarter of the winter months see less than 30 inches of snowfall, both mountains are well-protected, and the snow is preserved by summit elevations over 11,000 feet.
Double Diamond in downtown Aspen is a multileveled-multibar partying scene-to-be-seen extravaganza. Rub elbows and other things with Hollywood stars and starlets while being thumped by the best sound system in the Roaring Fork Valley.
"When it dumps, I head to The Dumps-a half dozen trails that really hold snow because they're east facing. Skier's left of S1 has a consistent fall line and a 40-degree pitch with a cliff band you can choose to hit or not to hit."