Aspen Bars & Nightlife
517 E. Hyman Ave., Aspen
The entire vibe in Aspen can get a little glitzy, which is exactly why a straight-up dive like Little Annie's is such a breath of fresh air. Don't bother looking at the menu—just do as the locals do and order the burger, fries, and a beer on tap.
330 E. Main St., Aspen
Situated in a side entrance of the historic Hotel Jerome, J-Bar has been a popular local hangout for years (Hunter S. Thompson famously made it his campaign headquarters when he ran for town sheriff). When Auberge bought the hotel back in 2011, it gave the space the expected makeover, but it's largely retained its charm. It remains cozy and dimly-lit, and its proximity to the base of Ajax and the rest of downtown Aspen makes it an ideal location for spiked hot chocolate after a long day on the mountain.
Cloud Nine Alpine Bistro
Aspen Highlands, Top of the Cloud Nine Lift, Aspen
A huge part of the appeal of skiing is the promise of the aprés ski scene afterwards, and this spot on the top of Highlands, conveniently equipped with bubbling raclette grills, is definitely the place to be at around 2pm. It's undergoing a controversial expansion right now, and while locals worry that too much space will ruin the charm, it hasn't slowed them down quite yet. Expect to see people on tables in ski boots until 4pm, when ski patrollers join the party and promptly kick everyone out. P.S. Champagne (for drinking or spraying) is definitely the order of choice here.
450 S. Galena St., Aspen
This legendary live music venue is the type of place that could only exist in Aspen: It's unimaginably tiny, it's always packed, and it brings some of the best musicians in the country to a small, isolated mountain town. The rumors about the big-name acts are no joke, as everyone from Wyclef Jean and Pitbull to SEAL, John Legend, and Lynyrd Skynyrd have graced the stage. With the exception of a few age restricted shows (check the calendar just to be sure), this is a family friendly spot, so whether you're seeing a local cowboy crooner or Widespread Panic, you can bring the whole group along.
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