Started in 2006 as 'Land Run 100' with 121 riders, 107 miles, 6,000+ ft elevation. Bobby discovered 'every direction two miles out of Stillwater we've got some of the best dirt roads on planet Earth.' Opened District Bicycles in Sept 2008. Renamed to 'The Mid South' in 2013. The finish-line hug tradition started year one—Bobby hugs every single finisher. 'I still need my Bobby Hug!' is a common refrain from returning riders who travel 1,000+ miles just for this race. The event grew explosively to 2,500+ today. Founded in 2006. By Bobby and Crystal Wintle (owners of District Bicycles, 712 South Main).
Reputation: The unofficial U.S. gravel season opener. Known for Bobby's finish-line hugs, unpredictable weather, iconic red clay, and one of gravel's strongest community vibes. The DFL (Dead F*cking Last) rider gets a giant steer skull trophy and massive celebration.




