Bobby Wintle
Known for his infectious enthusiasm, positivity, and commitment to doing the right thing, 2022 Gravel Cycling Hall of Fame inductee, Bobby Wintle, is a man of deep conviction. Through his event, The Mid South, and his local bike shop, Wintle has helped countless riders find their own love of gravel cycling.
Inspired by his experience at the Dirty Kanza 200 (now Unbound Gravel), as well as conversations with fellow 2022 Gravel Worlds Hall of Fame inductee, Chris Skogen, Wintle and his partner, Crystal, moved from their Kansas home to Stillwater, Oklahoma. There, they opened District Bicycles and started a gravel event of their own, the Land Run 100.
“Chris Skogen had an unbelievable influence on me from a distance, and he probably didn’t even know it,” Wintle said. “Thank you for your work, Chris.”
Wintle’s event was later renamed The Mid South, after he learned the original name could be seen as a barrier to participation.
“I am most proud of the change of our name and brand from Land Run 100 to The Mid South,” Wintle said. “At our absolute core, we want every single individual to feel welcome, safe, invited, and celebrated at our event.
“Changing the name removed a barrier for Indigenous individuals to feel welcome and comfortable at The Mid South.”
Wintle said he’s always been a person that doesn’t let things get in the way of what he wants to see happen, or what he wants to accomplish in life. The experience of seeing thousands of humans do things they weren’t sure they were capable of has taught Wintle that everyone is capable of doing great things.
“We are beautiful,” Wintle said. “We are worthy of love, and we should do hard things. When we do hard things, it shows us that we are worthy and capable of so much more than maybe we ever thought.
“It’s not about luck. It’s about believing it’s possible. Whether it’s a bike ride or building your business, or just getting out of bed in the morning. We are all capable.”
Wintle’s ‘Bobby Hugs’ for finishers crossing the line at The Mid South are nearly as legendary as the red/orange mud the early season event often features. The theme of unconditional love and acceptance Wintle weaves into his event has made it one of the most popular and enduring gravel events in the U.S. Each year, thousands of cyclists and their crews descend upon Stillwater to take a shot at The Mid South.
According to Wintle, the proliferation of gravel cycling has offered him the opportunity to travel to ride and experience parts of the world he never imagined possible.
“I’ve had the wildly beautiful fortune of watching people grow around me because of the ‘gravel scene’,” Wintle said. “It’s beyond explanation. The most beautiful people, the most beautiful friendships, and incredible conversations have happened because of all the different people, events and opportunities that have appeared along the way.”
