Before Matthew Bolick moved to Marfa over three years ago, he was organizing hardcore and punk rock shows and other music events in Austin, including a festival called Weekend at Larry’s, named after his burger pop-up, Bad Larryβs Burger Club. Heβs learned that producing a music festival in far West Texas is a whole different ballgame.
βTo decide to do a festival out here with the lack of infrastructure that we have, it takes a little bit of gumption or stupidity,β he says, βI donβt really know which one. Maybe a little bit of both.β
Despite the challenges, Bolick, who also owns Larryβs burger stand in Marfa, pulled off the Flying Island music festival last October, and it succeeded enough to bring it back for a second year Oct. 23-26. Twenty bands, including Tortoise, Combo Chimbita, and the American Analog Set, are scheduled to perform at five venues around town.
Frequent visitors to Marfa know that fall is filled with back-to-back events, such as Chinati Weekend, Marfa100, and Art Blocks Weekend. In 2024, a hole emerged when the team behind El Cosmico announced the hotel/campground was relocating, thus forcing its annual Trans-Pecos Music Festival of Love and Music to go on hiatus. Bolick initially thought about hosting his own festival with the idea to bring his musician friends to hang out and play music.
Kendall Craig, senior producer for Trans-Pecos Festival of Music and Love and owner of Stop & Read Books in Marfa and Austin, had a similar idea. She caught wind of Bolickβs intentions and reached out. Together, they started scheming about Flying Island, named after the jazz fusion band Bolickβs uncle played in the early 1970s. That Marfa is near the sky island of the Davis Mountains in Fort Davis makes the name all the more fitting. They brought in Lauren Dickens, a graphic designer, and Derek Brown, owner of the record label Hippie Scum and a DJ under the same name, to help behind the scenes.
β[Derek]βs just got impeccable taste, so he and I kind of split the booking on bands,β Bolick says.
Along with Trans-Pecos, Bolick drew inspiration for Flying Island from Ballroom Marfa and the Marfa Myths music festival, which the organization produced from 2014 to 2019. βNone of what weβre doing here, I feel like, would happen without that paving the way in a lot of ways, because people are looking for that sort of vibe out here, because of Marfa Myths, because of Trans-Pecos,β he says.

Last year, that vibe permeated the fest. Helado Negro danced across the stage during his solo set at then-open El Cosmico after Sessa warmed up the crowd with his free jazz and tropicΓ‘lia. Folk singers Ryan Sambol and Steve Gunn opened for Bill Callahan on a small stage at Larryβs, with shade structures keeping everyone cool on that sunny day. Thailand band Khun Narin completely won the crowd over during their show at Marfa Spirit Co.
For this yearβs event, Bolick reached out to Tortoise first. The β90s post-rock veterans are one of his favorite bands and to find himself in an email chain with drummer John McEntire, who Bolick admires as a fellow drummer, was surreal. El Cosmico is opening their small stage for Tortoise to play on Oct. 25, the day after their album, Touch, comes out, their first album since 2016.
Other artists appearing include The Egyptian Lover performing at Marfa Spirit Co on Friday night with John Carroll Kirby, TAKAAT, and local band Proxygente. Before that, American Analog Set and Dreamage are playing an afternoon show inside the arena at the Chinati Foundation, a new venue to the festival.
Every event Bolick organizes incorporates food, so there will be food popups throughout the festival. Larryβs will offer burgers and hot dogs while his buddy, Carlos Suarez, will serve Cuban sandwiches through his pop-up, Oye Chico. Chef Lauren Herrera, who has worked at Bad Larryβs Burger Club and Bummer Burrito, will wrap up the festival with a brunch on Oct. 26 at Planet Marfa.
Bolick felt like the organizers had four months to put together the inaugural festival, but it was a great first year with 600 people in attendance. He hopes to see more this year. However, he wants to focus more on dialing in the production rather than expand the festival during these early years. βWe truly love the intimate nature of the weekend and want to build on that over time,β Bolick says.
One thing to expect is a unique experience every year. βNo two fests are alike,β Bolick says. βThis one will not be like the last one. We do it again, it wonβt be like this one. Itβs always different.β
The full lineup and tickets for this yearβs Flying Island can be found at flyingislandmarfa.com.