Prior to March 2, 2018, flipturn had never played a festival and had hardly performed to a crowd of over 200 people.
When the band hit its first festival stage at 1:30 p.m. on that spring day eight years ago, many festivalgoers were still asleep. Lead singer Dillon Basse didn’t care. He said it felt like he and his band were playing Madison Square Garden.
The festival wasn’t at that famous New York venue, but rather four hours south of Basse’s hometown of Fernandina Beach, at the Okeechobee Music & Arts Festival.
Basse, 28, had known of Woodstock and other legendary festivals in documentaries. But actually playing one — at a time when Basse didn’t think fronting flipturn could be his career — was more than the then-sophomore at Jacksonville University could hope for.
Back when flipturn was playing house shows at UF, the band decided to enter Destination Okeechobee, a battle-of-the-bands contest where winners secure a spot on the festival’s lineup. Basse and his band asked their friends to vote, campaigned at their shows and received most of their support from the Gainesville community.
“This is only the beginning,” Basse told The Alligator after flipturn’s win in 2018. The band would go on to gain international recognition as renowned indie rockers, but they’d make sure to stop back at OMF in 2020 and 2023.
It was flipturn’s Destination Okeechobee set that made the difference, and the competition’s new wave of winners are already feeling its impact.
“It really just kept us wanting to keep pursuing music and pursuing the band,” Basse said. “Because the feeling of being up there on a stage, a festival stage specifically … you just felt like the dream was happening.”
Tattoos and tears of joy
Festivals like OMF expose performers to new crowds, Basse said. Of course, many festivalgoers this year have been following flipturn for a long time.
When Nicholas Schalk was in high school, his friends took him to St. Petersburg to catch a flipturn show. At the time, Schalk had never heard of the group.
The show was in the back of a brewery, and Schalk somehow got in for free. It was the “coolest thing ever,” he said.
Having now seen the Jacksonville-based band countless times, 25-year-old Schalk has a poppy flower and the words “six below” tattooed on his arm, both references to songs from early flipturn EPs.
“I've seen them since they were a baby band,” Schalk said.
The 2026 festival marked Schalk and his friend Sophia Guelfi’s first time at OMF. They traveled from Naples and arrived late Thursday night but still woke up first thing Friday to run in the OMF 5K Run.
Thomas Rowland is more than just a flipturn fan. He and his band, Winyah, were asked to cover “Inner Wave” on flipturn’s most recent album “Burnout Days (Reimagined).” The call from his manager breaking the news left Rowland in tears of joy.
Rowland, the 24-year-old frontman of his South Carolina indie southern rock band, took the “Now” stage nearly five hours before flipturn. To Winyah, being on flipturn’s album and on the same bill as the band at OMF felt surreal.
“It's always special to get to play in the same place as them,” Rowland said. “They have been a huge inspiration for us.”
At 6:45 p.m. Sunday, flipturn opened its set with “Inner Wave” as the Winyah members watched from the crowd. The sun was setting, and silhouettes of birds and hang gliders floated past.
During its 75-minute set, the band played hits like “Glistening” and “Moon Rocks” to a crowd that filled the festival grounds to the east gate.
A few songs into flipturn’s fourth OMF appearance, frontman Basse said to the audience that the band wouldn’t be what it is without the festival.
Far away from Philly
Hugh Hinton imagines winning Destination Okeechobee will be a major catalyst in his musical career, too.
Hinton, whose artist name is spelled “Hue Hinton,” found out about Destination Okeechobee through a friend. He shrugged it off and figured entering the competition would be a shot in the dark. But Hinton sent in a video, and before he knew it, he won this year’s competition.
The 25-year-old Philadelphia-based songwriter said his persistence secured him the victory; he texted everyone he knew to vote for him.
Members of his backing band, Greydyent, have played together for around a decade and are masters at their instruments, according to their friends. They attended the School of Rock in Berwyn, Pennsylvania, and have all practiced instruments for years.
Among them was bassist Timothy Chiles, a UF alumnus. Now Hinton’s roommate, Chiles has never seen anyone work harder than his singer, who heads to the piano after long days working as a music teacher and in a restaurant.
“When people ask about Hue, that's the first thing I say. That's the difference that sets people apart,” he said, “the ability to keep doing what you're doing every single day no matter what, and it's what he loves.”
“It doesn’t feel like work,” Hinton replied.
Hinton’s love for music began at a piano bench when he was 3 years old. Soon, he was singing in church choirs and playing pop-up shows at the Philadelphia Museum of Art. In 2021, he began releasing his own music.
“Starfish,” his Jan. 30 EP, took a year to make. Its music embodied resilience and stemmed from the feeling of trying to catch up in a fast-paced world, he said. He played several tracks from the project at OMF on Saturday during what marked his first-ever festival appearance.
“A lot of emotion went into writing this project, but to think that I was able to play it on this big of a stage,” he said. “If you told me that a year ago, I wouldn't believe you. But deep down, I always felt it should be heard by more people.”
Several of the band’s high school friends joined them on their almost 20-hour van ride south. They were among the first to arrive at its set at the “Aquachobee” stage.
They said it took more than the support of a few buddies from Philadelphia for Hinton to win Destination Okeechobee, though.
“He had all of the city backing him up,” his friend Phia McElgin said. “So I think he won because everyone loves him and his music and knows how talented he is and deserves this opportunity.”
Another friend of Hinton’s, Paige Junikiewicz, said OMF will mark a shifting point in the band’s career. Walking around the festival grounds, she encountered strangers who had Hinton’s set circled on their schedule.
“I think it's a huge break for them to have people hear outside of the Philadelphia area what's really going on,” Junikiewicz said ahead of Hinton’s set. “People are gonna be blown away today.”
Hinton and his band took the stage at 1:30 p.m. on the sunny Saturday afternoon. They had palm trees to their backs and a beach lined with hammockers and suntanners at their front. Donning shades and button-down short-sleeve shirts, Greydyent looked like Floridians.
They opened with “I Crashed My Car” — the first single off of “Starfish” — and closed with a cover of “Don’t Let Me Down” by The Beatles. Hinton jumped and screamed in a Jim Morrison-esque manner, breaking free of the quiet persona his friends say he maintains in day-to-day life.
Minutes after his set, Hinton said playing OMF was one of the peaks of his life.
Believing in herself and humanity
The other 2026 Destination Okeechobee winner, Carolina Calderon-Rueda, said the festival changed the trajectory of her life, too. But that started when she attended OMF as a timid festivalgoer.
Calderon-Rueda, a 24-year-old DJ from Miami who goes by La Combi, was anxious walking onto the festival grounds in 2022, surrounded by strangers. But her friend Sarah Ledezma, who joined her, saw her let her guard down and witnessed her fall in love with electronic music instantly.
Ledezma said Calderon-Rueda bought a DJ board as soon as she got home.
“She got sweat all over that deck,” Ledezma said. “She got glitter all over that deck. She played wherever she could, wherever anybody would listen, wherever anybody would connect.”
Reflecting on four years ago, when she and Calderon-Rueda set up camp at OMF with nothing but a stakeless tent, a pack of cheese and turkey, Ledezma said it feels full-circle to see her friend perform at the festival.
For Calderon-Rueda, there was a “before OMF” and an “after OMF.”
As a political science junior at Florida State University, she was unsure what she wanted to do with her life. She was lost and became angrier with injustices in the world as she delved into politics.
But OMF shifted Calderon-Rueda’s perspective on society. It helped her realize she could affect change though music.
“Coming to this festival restored my hope in humanity,” she said.
The DJ, who started out playing on her kitchen counter in her Tallahassee apartment, couldn’t foresee winning Destination Okeechobee. She posted her submission on the deadline, Feb. 13, and expected to hear nothing. An email came a week later.
Winning the competition made her realize just how large her support system is. Friends of friends of friends voted for her, as did relatives from Mexico and Costa Rica who she’s never met.
Around 10 members of that support system rushed backstage toward the end of Calderon-Rueda’s performance Saturday night. The DJ played an hour set of her signature Latin sounds while her 4’11” frame peeked over the flames that projected in front of her board.
Calderon-Rueda’s self-doubt melted away upon hitting the festival’s “Incendia” stage. She kept reminding herself that the universe wouldn’t have given her the opportunity if she wasn’t ready.
Like Basse said in 2018, Calderon-Rueda believes her OMF set was only the beginning.
Contact Isabel Kraby at ikraby@alligator.org. Follow her on X @isabelgkraby.
Isabel is the The Alligator's Spring 2026 music reporter. She is a junior studying journalism at UF and is from Ormond Beach, FL. In her spare time, she loves going to concerts, crafting and practicing guitar.
