The ski resort that celebrities visit but can never quite own

It takes about five minutes in Aspen to realise the town is nothing like its reputation suggests. Yes, there are private jets and $20,000 ski jackets – but beneath the gloss lies an enduring Colorado community, four genuinely world-class mountains, and a live music venue that draws the whole town in, private-jet crowd included

My friend Lea chastises me every time. “Just leave them there,” she tells me, referring to my ski boots that are standing against a fence beside the gondola in the middle of town. “No-one steals anything in Aspen.” 

She should know – she’s lived in the Colorado ski destination off-and-on for 30 years. I should too – I’ve been a regular visitor since 2004. For a decade, I didn’t miss a season. “Aspen’s just a little country town,” Lea says.

Never mind that every celebrity type, every corporate mogul and every wannabe descends on it, especially around the Christmas holiday season. Aspen is still, at its heart, the same humble ski village it always was. And that’s its appeal. Very showy people might come here, but Aspen itself is the antithesis of pretentious.

While You’re Here

Snowshoe with a naturalist through an 1800s ghost town of Ashcroft to Pine Creek Cookhouse for a gourmet lunch beneath 4,300-metre-high mountains.

Hear from some of the world’s most famous leaders at the Aspen Institute. Stay on property at Aspen Meadows and hike through 20 private hectares. 

Visit the 3,300-square-metre Aspen Art Museum, located in a dramatic Shigeru Ban building and dedicated to contemporary works.

Walk the John Denver Sanctuary on the edge of town (Denver is a former resident).

Childlike wonder

Aspen reminds me of my childhood town, Byron Bay… but with snow. Its past mirrors Byron’s – the domain of farmers and ranchers, Aspen became the gathering place of hippies and counter-culturists in the 1960s and ’70s. Money and famous people with even more money followed, but the alternative vibe of Aspen never changed. All it takes is the roll-out at a Grateful Dead tribute band at local live music venue, BellyUp, to be reminded. Forget all the private jets, Aspen is a chill town at heart.

“In Aspen you either have three homes or three jobs,” town historian Tom Egan says. “Most of us fall into the latter category; the rest fly around in their private jets and keep out of our way.”

A real town, not a resort

Created along the pretty Roaring Fork Valley, there’s not just one resort in Aspen, but four on the one ski ticket. Snowmass is one of North America’s largest, and Buttermilk is rated America’s best beginner mountain. Here, 160 years of history still stands on the grid of broad streets that constitute the town, many of them Victorian-era buildings from a prosperous silver mining past. You don’t get that in other Colorado resorts like Vail – which was never a town, just a Bavarian-themed ski resort conceived in the 1960s – or Beaver Creek.

Aspen’s uber-luxe offerings blend into its streetscape, overshadowed by mountains that are right there, casting shadows over the streets. I’m sure the look-at-me crowd must be disappointed by how understated expensive hotels look here. Even the most iconic, The Little Nell – Aspen’s only five-star, five-diamond property and its only hotel with ski-in, ski-out access to Aspen Mountain – feels more cosy than classy. 

Little Nell’s exterior is unassuming, and inside guests gather on low couches in a lounge off its lobby. When I visit, Elle Macpherson and pop star Gary Barlow are here relaxing, deep in conversation. Guests treat it like their private residence – dogs are allowed and staff don’t judge you based on what you wear. And while there might be US$50,000 bottles of wine offered in signature restaurant Element 47, there are none of the exclusionary five-star inclusions many other ski resort hotels are famous for. Opulence, in Aspen, is approachable. Outside, Ajax Tavern feels like a casual après bar… albeit frequented by people in $20,000 ski jackets.

Good to know

Consider Aspen’s shoulder seasons for less crowds, and better prices – go after Spring Break (mid-March) when the snow is still great but the temperatures are warmer. The best snow falls from late December to early April, but it’s best to avoid busy periods like Christmas and President’s Day Weekend (mid-February).

Fame is incidental

Too much talk of Aspen fixates on its regular celebrity visitors. But that is doing it a disservice. Encounters with A-listers are rare, and there is so much more to the destination than famous people (although Kevin Costner’s ranch, located just outside town, is worth a visit). At my other favourite lodging, Hotel Jerome, though, I can’t help but picture John Wayne and Gary Cooper drinking beside me at signature watering hole, J Bar, once Hunter S Thompson’s defacto office. It’s set in a three-storey, red-brick hotel built during Aspen’s silver-mining boom in the 1880s. After WWII, Old Hollywood took the hotel over, and now all of Aspen’s post-Indigenous history can be felt here. There’s a yesteryear grandeur, but it’s also very fun – it’s probably the only place in America bellboys can wear cowboy hats and not look kitsch.

Food has long been Aspen’s drawcard. In the Art Deco building next door to Hotel Jerome you’ll find speakeasy cocktail bar Bad Harriet. When I visit they serve a 13-course omakase tasting menu, part of a 14-week program by hot New York sushi restaurant Taikun Sushi. And just around the corner is the first Matsuhisa (from Japanese celebrity chef, Nobu Matsuhisa) to open outside of Beverly Hills, located inside a converted 120-year-old Victorian house. 

Each time I’m in Aspen I discover new restaurants. This time I fall for PARC Aspen and executive chef Mark Connell’s (ex-French Laundry) cast iron-seared steaks. And the best part is, I can eat at the bar in my ski clothes. On its Aspen’s mountains there are equally gourmet dining options at restaurants like Snowmass’s Lynn Britt Cabin. But every local’s favourite spot is Bonnie’s Restaurant, a rustic, timber-walled eatery where you line up for your meal. My first true ski crush destination may well be my tasty last.

Too much talk of Aspen fixates on its regular celebrity visitors. But that is doing it a disservice. Encounters with A-listers are rare, and there is so much more to the destination than famous people.

Journey Notes

There are direct flights from Los Angeles to Aspen. The town is located five kilometres from the airport. Check in to The Little Nell or Hotel Jerome. aspensnowmass.com colorado.com