The Aspen List

I’ve always had a soft spot for Aspen. I learned to ski there on a family trip in the mid-‘80s, staying slopeside at The Little Nell (not entirely coincidentally, my daughter is named Nell). This was long after the era MTV founder Tom Freston describes in his new book Unplugged as “a pirate hideout where skiing and hedonism were the prime pursuits”—where Hunter S. Thompson’s Freak Power party of “longhairs, heads, fun hogs, and weird night people of every description” very nearly took City Hall—but still comfortably before Gucci or Hermès put down stakes.

These days, I’m not sure I’d recognize America’s most famous frontier ski town (though I guess skiing and hedonism still drive the economy). Global luxury brands coexist with Aspen’s mountaineering DNA, and in peak season it’s entirely normal to see a Hollywood actor buying a matcha latte at Gorsuch Ski Cafe, or having a Stetson custom-shaped at Kemo Sabe between runs. In the intervening years, too, the growth of the Aspen Institute and Aspen Food & Wine turned the town into a year-round destination for ideas, elevated cultural events, and private jets, which now routinely outnumber commercial flights. 

And yet Maureen Poschman, a friend in hospitality comms who’s lived in Aspen for 35 years (and who was a huge help in wrangling this list!), reassures me that the former silver mining town still very much has a mountain soul, if you know where to look: “Aspen is still in essence a small town, surrounded by wilderness with the added appeal of fascinating people from all over the world. The outdoor adventures and the creative spirit of Aspen keep us connected and grounded. I’m always finding community here, whether it’s at an ACES event at the newly expanded Toklat Lodge near Ashcroft, at an Aspen Film premiere at the historic ISIS Aspen, at an après party on the roof of the Aspen Art Museum, or at breakfast at Bonnie’s on the mountain.”

The first thing to understand—especially in winter—is that “Aspen” unfolds across four distinct mountains, each with its own character. Aspen Mountain (Ajax) rises directly from downtown and is beloved for its steep, intermediate/expert terrain and ideal for strong skiers who want culture, great food and après within walking distance. Snowmass, the largest of the four, has reliable snow and terrain for every level, making it a great family-friendly option, especially if you stay at Snowmass Village for ski-in/ski-out access. Aspen Highlands tends to be a locals’ favorite, beloved for its hike to Highland Bowl, and suits advanced skiers staying in Aspen, just a short shuttle ride away. Buttermilk, known for its gentle slopes and terrain parks, is great for beginners and freestyle skiers and is easily accessed from Aspen itself. (NB: Aspen has a convenient bus system between the mountains and between Aspen & Snowmass.) 

In summer, staying in Aspen proper gives you true walkability to restaurants, shops and galleries (some hikes and bike routes start right from town or just beyond it), as well as proximity to festivals and performances; you may not even need a car if you avail yourself of the aforementioned bus system.

Whatever the season, Aspen has more variety than most mountain towns when it comes to eating, lodging, cultural explorations, and of course the skier’s happy hour—après. Some of the most visible spots can also get very crowded. So we asked a roster of well-connected locals and frequent visitors to share their insider favorites with us, and with you! —Alex Postman

ZACH WEISS – style/travel writer and head of brand for Outerspace 

“Aspen is one of my favorite destinations—I usually end up being lucky to go at least twice in the winter, and on occasion in the summer (which is also an underrated time to visit)! While there are plenty of fancy mountain locales in the Great American West, what I always say I love about Aspen is that everyone is in on the joke together. Whether they’re a longtime local or a first time visitor, Aspen leans into the absurdity of it all and the sort of aura that surrounds it thanks to unforgettable scenes in films like Dumb & Dumber. It’s where fur and diamonds and Western-wear and Prada ski suits all intermingle, and it’s the closest thing Americans have to Gstaad or St. Moritz.”

PRACTICAL INFORMATION 

Getting to Aspen is often not easy. The airport is located in the middle of several mountain ranges and, as expected, snow can often derail planes. With that in mind, I always try to approach the travel day with an outlook that no delays is a miracle, some delays are likely, and major delays may be par for the course.