You can't talk about Mid South without saying Bobby Wintle — Bobby, who also owns District Bicycles in Stillwater, personally hugs every finisher, from the elite winner to whoever crosses the line at midnight. Founded in 2006 as Land Run 100 with 121 riders and later renamed The Mid South, it's grown into one of the most beloved events on the American gravel calendar precisely because it never lost that personal, community-built feel even as the field grew past 2,500.
It was one or few marquee races to experiment with a pro-only race day (SBT GRVL and Sea Otter Classic) — elites raced Friday with the course to themselves, and amateurs followed on Saturday. The historically large pro presence produced a more modest elite field in 2026, but the event itself still sold out. This remains the first marquee race on the gravel calendar each year and is considered a genuine darling of the sport's original American gravel scene.
Oklahoma's red clay is the defining physical character of the race — locals call it 'The Mud South' in wet years, when the clay turns into a drivetrain-eating paste that reshapes the whole tactical picture of the race (see: the 2020 edition). Run in early March, it functions as the unofficial start of the American gravel season, and its unpredictable weather (mud, cold, ice, or a perfect blue-sky day) is part of what riders return for year after year.
Registration typically opens in the fall for the following March; the 100-mile distance has sold out within hours in recent years. The Mega Mid South ultra route uses a separate grand départ format run earlier in the fall.