Not Just a Haven for the Wealthy.. What Does This American City Hide Behind Its Luxurious Shine?

- Visitors often go to Aspen, Colorado, for its five-star hotels, upscale shops, and world-class ski slopes that have made it one of the most desirable luxury destinations globally. But if you stay a little longer, you will discover the artists, eccentrics, ski enthusiasts, and rebels who live here away from the glossy image.

It has been more than half a century since the famous American writer and former Aspen resident, Hunter S. Thompson, contributed to establishing the image of this city as an unexpected stronghold of counterculture through the "Freak Power" movement, attracting intellectuals, artists, and unconventional thinkers.

Aspen was originally a silver mining center before it began attracting creatives in the 1940s, when Walter and Elizabeth Paepcke helped establish cultural, intellectual, and athletic institutions that contributed to shaping the city's modern identity. Although Aspen today is associated in many minds with wealth and glamour, Thompson's rebellious spirit has not disappeared.

DJ Watkins is one of those who keep that spirit alive; he is a writer, art curator, and owner of a local gallery who has dedicated a significant part of his life to keeping the flame of counterculture burning. He says that rebels are those who do not want to live according to the ready-made American model, adding that Aspen has always attracted this type of people.

From his "Aspen Collective" gallery, located behind the historic Wheeler Opera House, Watkins showcases works related to Aspen's cultural past alongside pieces by contemporary artists from the Roaring Fork Valley. He also runs the "Fat City Gallery," a name inspired by the title that Thompson suggested for Aspen when he ran for sheriff in 1970.

Watkins does not deny the manifestations of consumption and material display that characterize modern Aspen, but he believes the picture is deeper than that. He points to a strong return of local culture, with spaces for artists, community centers for the arts, musical and theatrical performances, and design events led by a new generation.

A city made by eccentric characters, and despite its current reputation as a "playground for billionaires," Aspen has a long history of irony and not taking itself too seriously. In the 1970s, when the pedestrian area in the downtown was still under construction, some residents thought it resembled a bowling alley.

They decided to practice "bowling" using a beer barrel instead of a ball, while participants played the role of human "bowling pins." The same spirit extended to the mountains, where informal groups of skiers emerged with their own names and rituals.

One of these groups was known as "the Dogs," and its members would bark at those waiting in line for the lifts. The tradition continues, as a younger group today has chosen the name "The Freaks."

In the 1960s and 1970s, graduates, artists, and people seeking a life outside the traditional American mold arrived in Aspen. Thompson became the most famous face of the political "Freak Power" movement, while newcomers contributed to pushing for environmental protection, imposing building restrictions, and influencing the town's future.

The city of Aspen had a rent of $75. Tim Mooney arrived in Aspen in 1970 and rented a wooden cabin in the middle of town for $75 a month. Mooney worked as a ski instructor for 25 years, accompanying artists like Jimmy Buffett and John Denver on their musical tours, and then became a real estate agent.

However, in the 1970s, he was serving drinks at the "J-Bar" inside the historic Jerome Hotel, where Thompson was a regular customer. Mooney recalls that writer Thompson would sometimes arrive at noon with his mail and stay until dinner, and that Hollywood stars like Jack Nicholson and Michael Douglas would stop by to meet him.

But the personalities attracted to Aspen were not limited to writers and actors; they also included cyclists, mountain climbers, fishermen, and passionate adventurers. Although the average price of a single-family home in Aspen today exceeds $13 million, and winter hotel prices can exceed $1,000 a night, Mooney still sees young people arriving in the city the same way he did, taking temporary jobs and shared housing for the chance to be the first to hit the slopes on a morning covered in fresh snow.

Money and culture have always coexisted in Aspen, but the shift towards its current luxury identity accelerated during the 1980s with increased investments from major corporations. The culture of celebrity also changed; in the past, well-known visitors tried to blend in with the locals and not draw attention, whereas later a culture emerged based on visibility, photography, and showcasing.

However, local life has not disappeared; away from the luxury brand stores, there are thrift shops, art spaces, and simple restaurants frequented by residents year-round. What appears in the media, according to locals, often represents peak season and wealthy visitors, not the daily life of the local community.

Strangeness hides in plain sight, and in the residential neighborhoods of Aspen, you might see the famous "pickle" car, a uniquely shaped "Volkswagen Beetle" that was previously used by a local shop to deliver sandwiches, as well as a Ferrari. Near Buttermilk Mountain lies the magic mushroom house, an unconventional home that a Polish entrepreneur named Andrzej Olrych began building in 1973, partially inspired by psychedelic experiences.

The construction of the house, which spans about six thousand square feet, took six years and features curved walls, mismatched windows, and almost a complete absence of corners. On the main street, the "Grateful Deli" restaurant retains a 1960s vibe filled with intertwined paint colors and symbols of the "Grateful Dead" band, while simple places like "BUCK" and "Woody Creek Tavern" offer an alternative to the very stylish après-ski scene.

For Watkins, this culture does not conflict with the luxurious side of Aspen. He believes that the meeting of culture and wealth is precisely what has given the town its appeal and depth since the Paepke family envisioned it in the 1940s as a place that brings together artists and intellectuals around the philosophy of "mind, body, and spirit."

The mountains remain a fundamental element of this allure, attracting adventurers, nature lovers, skiers, and hikers, as well as creatives who come to Aspen to think bigger. The next generation, one day inside the Aspen Collective gallery, a young artist was preparing for a new exhibition when Watkins jokingly asked him if he was one of the "rebels."

Watkins says he has dedicated his life to preserving Aspen's history while also crafting an exciting future that embraces the radical existence and counterculture that have always been part of the place. Aspen's future will not necessarily resemble the days of writer Hunter S.

The economy has changed, the personalities have changed, and even the "rebels" themselves have changed. But perhaps this is exactly what makes Aspen... Aspen.

As Watkins says: "The most important, meaningful, and exciting things in life are still happening here. You just have to look for them a little harder."