Comedian Jay Gillespie worked the Denver standup scene for eight years before taking his act on the road in 2018, playing shows in New York, Los Angeles and the Pacific Northwest.
Now, he spends his nights talking to a webcam in a vacant Trinidad storefront in Southern Colorado. He says his career is going better than it ever has.
Sure, part of it is that his nightly, improvised online video stream “Cougar Nights” can be watched by anyone around the world. But, he says with Trinidad’s population hovering just under 10,000 people, his work stands out, and the locals are showing their support.
“I considered myself very funny, and there’s still 150 comedians funnier than me in Denver,” Gillespie said. “Here in Trinidad, I get to really be a part of the community, I’m visible … Everyone’s like, ‘Oh yeah, that’s Jay Gillespie. He’s our comedian.’”
Gillespie is part of an increasing exodus of artists, entertainers and entrepreneurs from Metro Denver looking to build Trinidad, near Colorado’s southern border, into a cultural hub with an altogether different identity from the state’s expensive mountain resort towns.
If moving to Trinidad was a trend before, it began picking up momentum even more so during the COVID-19 pandemic.
Untapped Potential
Trinidad Economic Development Director Wally Wallace made a living as an event organizer in Telluride before moving to Denver 10 years ago. He said he had blown by Trinidad many times while driving south on Interstate 25, associating the city with its prolific downtown marijuana industry catering to out-of-state customers or it’s long-held reputation as the “Sex Change Capital of the U.S.”
But, as Wallace toured the city’s downtown with a friend in late 2018, he immediately saw potential.
“These amazing buildings, these amazing views, like this town is incredible and totally empty,” Wallace said. “We started looking at the real estate prices and houses that would have cost a half million dollars in Denver were $150,000 here.”
So, Wallace purchased a house and moved to the city within two months.
Trinidad is one of the state’s oldest communities. Located along the historic Santa Fe Trail, the town was founded in 1862 after coal was discovered in the region. What followed was a boom and bust cycle that has long marked Trinidad with economic instability. It’s a cycle that leads up to this day, with the close-by opening of the state’s first new coal mine in nearly a decade just this month.
But, Wallace said he believes the town’s location presents a big opportunity in the entertainment industry that hasn’t yet been realized. He said more vehicles come into Colorado at I-25 in Trinidad than any other roadway. The town also marks the midway point between Chicago and Los Angeles on Amtrak’s Southwest Chief line. Wallace used that last distinction for his first economic development project, where he brought comedians into the city on the train for a three-day bike and comedy festival in 2019.
Not long after, Wallace convinced his friend and one-time Denver mayoral candidate Kayvan Khalatbari, to consider Trinidad for some property investments. Khalatbari, an entrepreneur who became wealthy in the early days of Colorado’s marijuana industry, has spent millions in the last year buying more than a dozen properties in downtown Trinidad and nearby Raton, New Mexico.
Working alongside famous Denver preservationist Dana Crawford, he’s hoping to bring new tenants into long-shuttered downtown storefronts. He’s already announced a coffee shop, a brewery and a pizza place he does business with in Denver will all be opening new Trinidad locations in the next year.
Khalatbari is also renovating a downtown church into a new primary residence. He’s one of more than 20 friends Wallace said he’s convinced to relocate to Trinidad since moving here himself.
Staying Affordable
Hailey Bearden, 28, moved to Trinidad from Austin more than four years ago looking for a fun, artsy community where she could afford to live. She works at a downtown jewelry store and dreams of one day making a career out of her poetry. She said she has felt a growing buzz about the town since she arrived, but that it feels exponential since the start of the pandemic.
“Main Street is popping these days. It’s crazy, like, you have to wait at a stoplight. Four years ago, you didn’t have to wait at a stoplight,” Bearden said. “There’s so many people who are moving here. It’s almost like you can’t keep track.”
Bearden spoke from the back patio of the Trinidad Lounge, a historic bar recently reopened after a nearly decade-long closure, by Curtis Wallach and Suzanne Magnuson, the married owners of the Hi-Dive, a popular alternative music venue on Denver’s South Broadway Avenue.
Wallach and Magnuson put in new sound and lighting systems on the lounge’s stage and are looking to cultivate Trinidad as a place for bands to stop on their paths between Denver and venues in Texas, New Mexico and out toward the West Coast.
Wallach said they made the move to Trinidad to make the sort of impact they no longer feel they can make in Denver.
“Those places (like the Hi-Dive), can’t touch the cultural fabric anymore. The cultural fabric of the city has gone beyond that, and I feel like Denver outgrew us in some ways,” Wallach said.
Magnuson said she hopes businesses like the lounge can help shake Trinidad from it’s boom-and-bust cycle and usher in a more sustainable long-term future that keeps the community in mind.
“I’m hoping that as we grow down here that we can do it in a way that’s consciously done so that we still have affordable housing. I don’t want it to spiral out of control,” she said.
Wallace said his biggest challenge is keeping living costs in Trinidad from following the same patterns seen in Colorado’s other growing mountain communities. His office has put out a request for proposals on how to best approach the issue long-term. And Kayvan Khalatbari said he plans to develop affordable housing options on six of the properties he has purchased in the city.
“(We don’t want to) lose the history or the culture of Trinidad, that it doesn’t go the way of other Colorado mountain towns and become this inaccessible, unaffordable place as recreation grows there.”
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