Bobby Wintle built The Mid South around bikes. He built it around music, too.

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

Quincy Einstein

Mar 10, 2026 - 7 min read

Bobby Wintle, who has built The Mid South's music programming into a cornerstone of the festival, performs on stage during the 2024 event in front of District Bicycles at the corner of W. 7th Ave. and S. Husband St. in downtown Stillwater. – Photo by 241 Photography

Bobby Wintle built The Mid South around bikes. He built it around music, too. — Bobby Wintle, who has built The Mid South's music programming into a cornerstone of the festival, performs on stage during the 2024 event in front of District Bicycles at the corner of W. 7th Ave. and S. Husband St. in downtown Stillwater. – Photo by 241 Photography

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.

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