It's a toss-up which sport is more popular in Aspen, celeb-spotting or skiing. The good news is that one is free, and the other doesn't have too hefty a price tag. Aspen Skiing Company operates the four mountains in the area--Snowmass, Buttermilk, Aspen Highlands, and Aspen Mountain, also called Ajax. The monopoly works in visitors' favor. A multiday lift pass is good at any mountain, and a free shuttle, which loops around the four ski areas, makes traveling between them pretty simple.
Timing your trip can be puzzling. Aspen Central Reservations, the official reservation service, divides winter into six seasons: Thanksgiving, Early, Holiday, Value, Peak, and Late. Early and Value--basically the months of December and January, excluding holidays--have ideal conditions and prices. A six-day Early Season lift ticket is $408, $36 less than in Holiday Season. And ACR's website also lists last-minute packages.
When it comes to day passes, an afternoon half-day ($59) may seem like the smart way to go, but skiing a morning half-day ends up being the same price--and more appealing. A program called First Tracks lets you claim a spot on the next day's 8 a.m. Ajax gondola. You'll be paving your way through fresh snow in relative quiet. Then, turn in your pass before 12:30 p.m. to get a $19 rebate.
In any town where $1 million doesn't even buy a teardown, finding a reasonable place to stay is the true challenge. Surprisingly, Aspen has fine options, all within walking distance to the mountains or shuttle. The best bargain is a bunk in a two- to four-bed room at St. Moritz Lodge--it starts at $31 a person, though your roommates could be strangers. There are also one- and two-bedroom condos for families (from $128). Everyone has access to a steam room and pool; the free breakfast consists of bagels, waffles, and hard-boiled eggs. The lodge also has a locking indoor ski rack for your gear. For longer stays, the Chalet Lisl rents quaint studios (from $119) and one-bedroom apartments (from $150), both with full kitchens.
Eating well is just as easy. Ajax Tavern doesn't charge an après-ski minimum, so you can rub elbows with the fur-trimmed starlets at outdoor tables. Little Annie's is far more casual; the barbecued beef sandwich with fries makes a hearty meal ($9). Cache Cache is one of Aspen's posher restaurants, but there's a well-priced bar menu--rainbow trout in a citrus vinaigrette comes with jasmine rice and is $12. Everyone and his arm candy ultimately ends up at Cooper Street, waiting for a turn at the pool table. It's just one more spirited sport in town--and best of all, it only costs five quarters.