Bobby Wintle on music, rhythm, and The Mid South

As The Mid South, a weekend endurance festival, prepares to unleash thousands of gravel grinders onto the dirt roads of Stillwater this weekend, founder Bobby Wintle is thinking about more than just finish times and course conditions. He's thinking about rhythm.

It's a few days before chaos descends on the small Oklahoma town. Professionals have already started rolling in — 40 of them hit the course yesterday for a pre-ride. Wintle's phone is blowing up with texts and DMs. But when we sit down to talk about the music side of the event, his energy shifts. His eyes light up. This isn't just a box to check on the festival planning spreadsheet. This is personal.

"The Connection Is Rhythm"

Q: What's the philosophy behind having such a strong musical component at an endurance race?

"I figured this out a long time ago," Wintle says, leaning forward. "There is this wildly overwhelming connection between musicians and cyclists."

He's thought deeply about this. For Wintle — a former musician who once chased the dream, recording an album and touring before life pulled him toward bikes and business — the answer is almost spiritual.

"I think the correlation is rhythm," he explains. "When you're riding your bike or running, you're doing something that requires repetition, energy, exertion. If you fall into a rhythm while doing that, it makes it easier. Cycling is a circle. It's a circle. It's like when you have the right BPM, the right backing behind you — it enhances your experience."

Raised on Dire Straits, Pink Floyd, Jethro Tull, and '90s country, music was always going to find its way into whatever Wintle built. When he and his wife Crystal Wintle started writing the business plan that would eventually become District Bicycles and then The Mid South — which the two co-own and co-direct — the decision was non-negotiable.

"It just had to have music. There was no way I was going to create something in my life that didn't also include music."

Bobby Wintle stands at a microphone in front of an outdoor tent stage at night while band members set up equipment behind him, with a brick building visible in the background, during the 2013 Land Run 100 in downtown Stillwater, Oklahoma. — Bobby Wintle addresses the crowd in front of the 7th Ave. stage as Colourmusic — the Stillwater-born psych-folk band — sets up behind him during the 2013 Land Run 100, an early iteration of what would become The Mid South. – Photo by 241 Photography

But it's more than personal indulgence. Wintle believes The Mid South's secret weapon is music.

"Everyone loves music — 99% of humanity connects to it. It's something people can connect with even if they don't know anything about the cycling world, the gravel scene. Music differentiates us from a lot of other events."

Booking Friends, Not Playlists

Q: How do you curate the lineup?

"There's no specific formula," Wintle admits. "It's always just been based on relationships."

He's maintained friendships with bands across the state and beyond — Owen Pye from St. Louis, Carter Hulsey from Nashville. But his heart is firmly planted in Oklahoma's burgeoning music scene.

"Everyone thinks Nashville is Nashville, Austin is Austin. But Tulsa? Tulsa rivals it. The music coming out of there is incredibly sick. I've always wanted to highlight local."

Scenes from the music stage at The Mid South 2022, three years before the festival's music would return to the block 34: Soup, left, and Bobby Wintle rides a bicycle on a trainer while Colourmusic plays. – Photos by 241 Photography

The Mid South lineup reads like a who's who of Wintle's personal playlist: Soup, Johnny Mullenax, Belle and The Vertigo Waves. He's watched friends evolve in real time.

"Johnny Mullenax — I've watched him go from playing every single night in different groups, backing people, playing with John Fulbright, then heading up his own thing, the creation of Bluegrass Brunch. Now he's been in Rolling Stone, signed to Billy Strings' management company."

This year, he's throwing in a curveball: Dreamsickle, a local band that's "totally different than any band we've ever had." When team members questioned whether they'd fit the vibe, Wintle's response was immediate.

"Yes, they're gonna fit. They asked if I wanted them to play a more chill set. I said absolutely not. I want you to destroy the stage."

Dreamsickle plays Block 34 Saturday at 5 p.m.

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When Music Meets the Finish Line

Q: Any memorable moments where music and race synced up?

Wintle gets quiet for a moment. Then he starts talking about the finish line.

"So many moments. More moments at the finish line than I could ever tell you."

This year marks a significant change: after 13 years, they've moved the finish line right next to the Block 34 and the Kicker Soundstage. It's intentional. Wintle wants the overlap.

"I'm there for every single person, hugging every finisher. The things people tell me — their motivations for why they're there, what pushed them through, what they've been through the last year. And the music being right there..."

He stops. Tears well up. He waves it off.

"I can't help it, man. It's insane."

He describes watching exhausted riders roll down the finish chute after 50 or 100 miles, live music washing over them, the announcer calling their names, bands interacting with riders as they pass the stage.

"It's like everyone's locked in. Everything's insane. I've burst into tears more times when live music is playing than when we just have a playlist going."

One moment stands out: Belle and The Vertigo Waves playing years ago as riders crossed the finish, and singer Belle Scott started talking to them mid-song. "It was like — okay, the band is not only here creating this experience, but they're straight-up interacting with the riders as they cross by the stage."

Belle and The Vertigo Waves play Block 34 Saturday at 8 p.m.

Bobby Wintle, wearing a District Bicycles T-shirt, dances at a microphone stand on an outdoor stage while a musician in a wide-brimmed hat stands behind him, with a crowd of festival attendees visible in the background. — Bobby Wintle dances on the 7th Ave. stage alongside Brahmulus — the lo-fi future soul project of Greg Brookshire — during The Mid South 2024. – Photo by 241 Photography

"They Didn't Buy a Ticket to See You"

Q: Does playing The Mid South offer a different experience for musicians compared to a club gig?

Wintle laughs. "The band knows everyone's here for a bike race. It's in the back of everyone's mind — they didn't buy a ticket to go to the show."

But that's precisely what makes it special. The musicians are performing for an audience that's exhausted, elated, covered in mud, or waiting for someone who is. There's an authenticity to it that club shows can't replicate.

His hope is that the line is blurring. Block 34 is a public park, which means the city can't require tickets for events held there — and with 3,638 participants registered to race this year, the built-in crowd is already significant. With perfect weather forecast and the Expo free to the public — featuring food trucks from Andolini's and Pasa that "nobody else is booking, ever" — Wintle wants Stillwater to show up.

"Come hang out. It's gonna be so sick."

Don't Miss: Sets and Future Dreams

Q: Any artists you're personally excited about?

"Matthew Scott," Wintle says without hesitation. "He's like Stevie Ray Vaughan incarnate, late 20s out of Guthrie."

Scott runs a YouTube channel about vintage guitars and might be bringing his '57 Gold Top Les Paul to the stage. "He rips. If you're into blues, rock and roll, southern rock — don't miss him."

The can't-miss moment? Friday afternoon, as the pro men's, women's, and non-binary finishers roll in between 5:30 and 6 p.m.

"Johnny Mullenax will be on stage. I put him there on purpose. That is deeply curated. I wanted Johnny for potentially the biggest crowd. He's going to bring this place together. He's going to shred."

Johnny Mullenax plays guitar on stage during the 2022 Mid South. – Photo by 241 Photography

The Future: Half Music Festival, Half Endurance Race

Q: Where do you see the music evolving?

"You're already seeing it," Wintle says. "There's so much of Mid South that could turn into half music festival, half endurance festival. This year, it's starting to look like that a lot more."

He envisions a future like Dancing Turtle — an arts and endurance festival that launched in June 2023 — "all an incredible amount of fun."

The challenge is financial. The music is folded into the experience for the 3,638 participants registered to race this year. Some events have found workarounds — Dancing Turtle, for example, designated VIP lawn zones in 2025 that required a donation to access — but Wintle is still working through what that could look like for The Mid South.

"I want to grow the music side. I want to figure out how to justify the cost of production, booking bands, hospitality — things I love almost more than anything. Could we get someone like Wyatt Flores? Could we figure out the financial end of booking names that are wildly recognizable?"

For now, he's focused on this weekend. On the rhythm. On the moments when an exhausted rider crests the finish line just as a band hits the perfect chord.

"I figured out a long time ago that music moves us. And movement — cycling, running, pushing yourself — it's all connected. That's what Mid South is. Connection."