Trail Running calendar near Oakwood 2025-2026

The Grind on the Grid Backyard Ultra is an exciting running event set in Veedersburg, Indiana, designed for endurance athletes. Participants will tackle a unique 4.167-mile course that combines gravel, grass, and road surfaces, with a focus on completing as many loops as possible within an hour. The..

The Hawthorn Half Day Relay & Ultra is an exciting endurance event taking place in Terre Haute, Indiana, established in 2006. Participants can choose between 6-hour and 12-hour races, with options for solo runners, teams of various sizes, and walkers. The course features a scenic 5K loop of trail an..

Glazin' the Trail is a family-friendly run/walk event taking place at Kankakee Community College in Illinois. Scheduled for May 31, 2025, this fun-filled morning features a donut-themed atmosphere, encouraging participants to enjoy the scenic trails along the Kankakee River. The event includes a 5K..

The Trail Trot Cross Country 5K and Kid's Fun Run is an exciting running event taking place at the Crawford County Recreation Center in Robinson, Illinois. This inaugural event features a 5K cross country race that traverses the scenic Lincoln Trail College campus, primarily on grass with some paved..

The Elsa Chicken Plucker Backyard Ultra is an endurance trail running event held at Willenborg Woods in Charleston, Illinois. Participants run a 4.167-mile loop every hour, with the goal of completing as many loops as possible. The event fosters a community atmosphere, emphasizing fun, challenge, an..

The Vulture Vista Ultra is an exciting running event set to take place at DePauw Nature Park in Greencastle, Indiana. This year, the event features multiple challenges, including 6-hour and 12-hour solo and relay races, as well as a 4.5-mile challenge designed for runners of all abilities. Participa..

The Dino Griffin 10K Bonus Run is a trail race held at Griffin Bike Park in Terre Haute, Indiana, on August 2, 2025. The race features a two-lap course around Stryker Lake with moderate terrain, rolling hills, and wide paths suitable for passing. Participants can earn bonus points toward the series..

The Kennekuk Road Runners - Wild Wild Wilderness is an annual running event held in Oakwood, Illinois, featuring a variety of races including a 5K, a 7.45-mile trail run, and the WWW Challenge. This event celebrates community spirit and resilience, welcoming both seasoned runners and newcomers. The..

The Shake Your Trail Feather Trail Run is a scenic trail running event held at Willenborg Woods in Charleston, IL. Participants can choose from various distances, including a 5K, 10K, half marathon, and 50K ultra, with races starting early in the morning. The course features technical single-track t..

The Allerton Park Trail Run, organized by the Second Wind Running Club, takes place at the scenic Robert Allerton Park in Monticello, Illinois. This event features a challenging 5.7-mile trail run and a 2-mile nature walk, allowing participants to enjoy the beautiful natural surroundings. Proceeds f..

The OPSF 50/50 Trail Race is a longstanding Indiana event held in Owen-Putnam State Forest, organized by the Indiana Trail Running Association. It offers multiple race distances, including a 50-mile, 50K, 14-mile, and 10K trail run, featuring challenging single-track and horse trails with rolling hi..