Here’s the thing about Aspen: No matter who you are or where you’re from, most everyone is here for the same thing—a taste of the ultimate ski-town dream, which Aspen serves up in in spades. The town delivers some of the best skiing (5,300 acres of inbounds terrain over four mountains), nightlife, and dining in the country. Hit Ajax for thigh-burning cruisers and the Highlands for steep skiing and a laid-back local vibe. But save some energy: When the lifts stop spinning, that’s when things really fire up.
Here’s your road map to the best Aspen has to offer—in a weekend or less.
About a five-minute walk to the gondola, the Limelight Hotel delivers the best overall value and vibe in town. Board games, a fleet of cruisers, and two hot tubs are at guests’ disposal. A tasty complimentary continental breakfast is served each morning. And you don’t have to go far for après—from 3 p.m. to 7 p.m. each day, the Limelight serves up a bar menu with wallet-friendly prices, live music, and one of the best après scenes around.
Meet at the gondola at 8 a.m. for First Tracks, a complimentary program for ticket holders that allows 15 skiers on the hill before the mountain opens to the public at 9 a.m. Lap miles of corduroy or lace figure eights through virgin snowfields while the rest of Aspen is still in bed. Sign up at the ticket office at the gondola base station 24 hours in advance to lock your spot.
Jump on the Ajax Express lift on Aspen Mountain and take it to the top of the mountain. From there, head right over to Walsh’s, an east-facing double black diamond run that gets tons of morning sun, which makes for great powder turns or corn skiing.
Don’t forget to hit Aspen Highlands. Head straight for the Highland Bowl, some of the best lift-accessed skiing in the Lower 48, via the Deep Temerity lift or Lone Peak chair. From there, jump on the cat for a boost a third of the way up, then begin the 40-minute bootpack to the top. Trust us, it’s worth it: 2,500 vertical feet of perfectly pitched, wide-open bowl skiing awaits.
For one of the best breakfasts in town, head to Bonnie’s. Beloved by locals and located on Aspen Mountain, this eatery serves up dynamite oatmeal pancakes and apple strudel.
Come lunchtime, head to the foot of Aspen Mountain and post up at Ajax Tavern. Grab an Ajax Double—the best damn burger in town. If it’s warm, also grab a seat on the sun-drenched deck and watch as wealthy cougars mix with celebrities and colorful locals like Benny the Blade, an Aspen icon often spotted sporting a fanny pack and his signature shaggy blond mane.
You can also try the newly renovated Merry-Go-Round, a popular mid-mountain lunch spot where you can grab quick organic bites. From there, point it to the parking lot and hightail it home.
When the dinner bell rings, head to the ski-in-ski-out Pine Creek Cookhouse for one of the best dining experiences in the Rockies. Found in the old mining town of Ashcroft, about 30 minutes from downtown Aspen, Pine Creek serves up killer food in a cozy log cabin with a roaring fire and views of the Elk Mountains. Park at the top of Castle Creek Road, then snowshoe, cross-country ski, or ride a horse-drawn sleigh to the Cookhouse.
Rehash and recover from the night’s antics over homemade doughnuts and blueberry pancakes at Main Street Bakery, the best breakfast joint in town. This place is what all breakfast spots should be: downhome vibe, awesome grub, and friendly service. Main Street Bakery gets slammed, so go early.
As you roll into town, stop at the Woody Creek Tavern, the old stomping grounds of Hunter S. Thompson, the legendary gonzo journalist who ran for sheriff of Pitkin County in 1970. About 15 minutes down valley of Aspen and festooned with Christmas lights and photos of regulars, Woody Creek is a funky dive bar that serves up killer burgers, anything from canned to draft beer, and a taste of old-school Aspen.
Après options abound in Aspen. For a rowdy singles scene and scantily clad snow bunnies in hot tubs, try 39 Degrees at the Sky Hotel. For more than 200 craft beers on tap (including Colorado classics like Telluride Brewing Co. and Upslope), a cozy fireplace, and American comfort food, head to HOPS Culture, a recently opened pub that’s on track to becoming an Aspen drinking institution.
With its A-list roster of talent, intimate setting, and great sound system, Belly Up is one of the best live music venues in the country. On any given weekend, Chromeo, Spearhead, or Taj Mahal might be headlining. This is the kind of place where rock and roll memories are made.