aspen, colorado —
Visit the five-star hotels, luxury boutiques, and world-class ski slopes that make Aspen one of the world’s most desirable luxury destinations.
Look out for artists, eccentrics, ski enthusiasts, and freaks hiding in plain sight.
It’s been more than half a century since famed American author and former Aspen area resident Hunter S. Thompson’s Freak Power movement defined this Colorado ski area as an unlikely countercultural outpost for intellectuals, artists and unconventional thinkers.
The former center of silver mining first attracted creative minds in the 1940s, when influential art enthusiasts Walter and Elizabeth Pepke founded the Aspen Institute and helped found the Aspen Ski Company.
Despite modern Aspen’s reputation for glitz and glamor, Thompson-esque freaks are still here.
DJ Watkins is one of them.
“Freaks are people who don’t want to live the traditional, cookie-cutter lifestyle of suburban America,” says Watkins, a local writer, curator and gallerist who has made it his life’s mission to keep Aspen’s counterculture flame alive. “And Aspen has always attracted people like that.”
From the Aspen Collective Gallery, located behind the historic 19th-century Wheeler Opera House, Watkins is exhibiting work related to Aspen’s counterculture past, along with contemporary artists from across Western Colorado’s Roaring Fork Valley. He also runs the Fat City Gallery (named after the nickname for Aspen that Thompson proposed when he ran for sheriff in 1970) and has worked to connect Aspen’s galleries through the Aspen Art Walk.
Watkins readily acknowledges the “conspicuous consumption” and “materialism” associated with modern Aspen. But he says there’s more to it than that.
“There’s a resurgence of local culture happening right now,” he says.
Watkins also points to a series of venues that carry Aspen’s creative heritage to this day. Buckhorn Public Arts has converted a former commercial space into artist studios alongside Eddie’s, a restaurant and market popular with locals. The city-run Red Brick Center for the Arts offers community classes and studio space, and the Paul JAS Center and Wheeler Opera House bring world-class performances to the city at affordable prices. Watkins also points to community events like the Aspen Design Conference as evidence that a new generation is putting their own stamp on Aspen.
Despite its modern-day reputation as a “billionaire’s playground,” Aspen has a long history of not being taken too seriously.
For example, consider the art of “mall bowling.”
When bricks were being laid for a pedestrian mall in downtown Aspen in the 1970s, members of the completely fictional Aspen State Teachers College (founded on a joke that Aspen resembled a college campus) decided the unfinished area looked too much like a bowling alley, said Aspen Historical Society archivist Anna Lucaville.
Naturally, they went bowling…even staged a 7-on-10 split in front of the camera using beer kegs as balls and the “students” as human bowling pins.
The same irreverent attitude reached the mountains, where loosely organized ski gangs developed their own names and rituals. One of the groups, the Dogs, was known for barking at people in the lift line. And that tradition is not just historical. Today’s Aspen’s young ski gang has adopted perhaps the most fitting name of all: the Freaks.
But that enduring playfulness coincided with more profound cultural changes.
In the 1960s and ’70s, college-educated newcomers, artists, and others came to Aspen in search of a way of life outside of the traditional American mold. While Thompson became the most recognizable face of the Freak Power political movement, Lookabile describes a broader “changing of the guard” as political newcomers pushed for environmental protection, zoning regulations, and greater influence over Aspen’s future.
Tim Mooney arrived in time to see everything.
He moved to Aspen in 1970 and rented a log cabin downtown for $75 a month. More than half a century later, he still lives there.
Mooney taught skiing at Aspen Mountain for 25 years, worked as a tour manager with singer-songwriters Jimmy Buffett and John Denver, eventually became a real estate broker for Christie’s International, and now jokes that Aspen Mountain’s gondola is his office.
But back in the ’70s, he was serving drinks at the J Bar, a historic watering hole inside the Hotel Jerome. Built in 1889, Hotel Jerome is an upscale Aspen landmark that has long attracted an eclectic mix of locals, celebrities, and big-name characters, including Hollywood stars such as John Wayne and Gary Cooper.
“I was kind of Hunter’s bartender for a long time,” he says, recalling how Thompson would arrive with the mail around noon and sometimes stay until dinner. Jack Nicholson stopped by to hang out with Thompson, as did other celebrities like Michael Douglas and Clint Eastwood, Mooney recalls.
People drawn to Aspen were not limited to writers and movie stars. Mooney remembers the rock climber, whom he describes as an avid cyclist, an “incredibly avid fly-tying enthusiast,” and simply a “monster of the mountain.”
And he sees younger versions of the same type arriving today, even though the current median price for a single-family home in Aspen is more than $13 million and average winter hotel rates can exceed $1,000 per night.
“We have people here who are willing to do odd jobs and live with roommates, just like I did when I graduated from college,” Mooney said. If that means being “first in the gondola line on a powder day.”
They sacrifice other parts of their lives for the mountains and “the spiritual atmosphere of being in this magical valley,” he says.
“You can live between the lines,” he says. “You can survive even in the middle of nowhere.”
Wealth and culture have long coexisted here. But Lookaville traces Aspen’s major transformation to its modern upscale identity in the 1980s, when large corporations increasingly began investing in the town.
Celebrity culture has also changed. Lookabile said famous tourists once came to Aspen looking to blend in with the locals, “not necessarily wanting to be seen,” but in the decades since, more flamboyant celebrities and influencers have arrived, “wanting to be seen and photographed.”
The existence of ski enthusiasts in the early days was also not as easy-going as myth suggests.
“Even back then, people were working hard to make ends meet,” Lookabil said. He himself recalls working multiple jobs after moving to Aspen 26 years ago.
There are fewer locally owned businesses now, but many workers live further into the Roaring Fork Valley and commute into town, she said. But Lucaville rejects the idea that the local community disappeared before Gucci, Chanel and Kemosabe. After all, Aspen also has its own volunteer-run Aspen Thrift Shop, where discounted items are readily available.
What you see in the media is “busy season,” she says. “And you’re looking at visitors. You’re not looking at the local community year-round. We’re doing our own thing on a regular basis.”
Some of that “mine” is hidden in plain sight.
On Aspen’s residential streets, you’re just as likely to see a Pickle Car (a quirky Volkswagen Beetle that once served as a delivery vehicle for the now-defunct local sandwich shop Johnny McGuire’s) as you are a Ferrari.
Near Buttermilk Mountain is the famous Magic Mushroom House, an unconventional home built by Andre Ulrich in 1973, inspired in part by psychedelic mushrooms and LSD. The nearly 6,000-square-foot home took six years to complete, with curved walls, mismatched windows, and virtually no corners.
The laid-back Grateful Deli on Main Street wraps your neighborhood sandwich shop in the Grateful Dead’s iconic tie-dye. Meanwhile, no-frills hangouts like BUCK and Woody Creek Tavern (where Thompson was once a regular) offer alternatives to Aspen’s more sophisticated après-ski scene.
For Watkins, none of this goes against Aspen’s luxury side. In fact, he argues that culture has always been matched by wealth, adding a “layer of depth” that other resort cities simply can’t replicate, as part of what made the town so attractive in the first place.
The idea dates back to the 1940s. The Pepukus envisioned the postwar town as a gathering place for artists and intellectuals organized around the “mind, body, spirit” philosophy that became known as the Aspen Idea.
What made Aspen a popular destination for the “more privileged,” Watkins said, is the fact that it has an “embarrassingly rich culture,” with a concentration of music, art, dance and performance.
Mountains are also a key part of the attraction, drawing what Watkins calls “an adventurous crowd interested in nature, skiing and hiking,” as well as creative people who come here “to think about bigger things.”
On a recent afternoon at Aspen Collective, the young artist was preparing his work for an upcoming exhibition when Watkins spotted him and turned around with an important question.
Was he perhaps a weirdo?
The artist did not hesitate.
“Yes, definitely.”
“All the freaks are going to be there,” Watkins said with a smile at the opening the next night, when young local artist Fat Chance will perform.
“I’ve kind of dedicated my life to keeping history alive,” Watkins says, “but also building a future that’s fun and embraces this radical counterculture that’s always been here.”
Its future is unlikely to be exactly like Thompson’s Aspen. Economics is different. The characters are different. Even freaks are different.
But maybe that’s what makes Aspen Aspen.
“More important, meaningful, exciting things in life are still happening here,” he says. “I’ll have to look a little more carefully.”
