Trail Running calendar near Oakwood 2025-2026

The Allerton Races is a running event taking place in Monticello, Illinois, featuring a variety of races including a Half Marathon, 10K, and a nighttime Trail-Glo 5K. Participants can also choose virtual options for each distance. This event not only promotes fitness and community engagement but als..

The DINO Trail Run in West Lafayette, Indiana, is set to take place at the Tippecanoe County Amphitheater Park on April 19, 2025. This event features two main race distances: a 5K and a 15K trail run, along with a free kids' race. The course is designed to be beginner-friendly, consisting of three l..

The Wabash Valley Road Runners - Swamp Stomp is an annual running event taking place in Terre Haute, Indiana, featuring a 5-mile run, a 4-mile walk, and a 1-mile fun run. Set in the scenic trails of Hawthorn Park, participants can expect a well-marked course with ample volunteer support. The event e..

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..

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 exciting trail running event set in the scenic Willenborg Woods in Charleston, IL. Participants will tackle a 4.167-mile loop every hour, with the last runner standing earning a Bronze Ticket to the prestigious Big Dog's Backyard Ultra World Championship..

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 Griffin 10K Bonus Run is an exciting trail running event scheduled for August 2, 2025, at Griffin Bike Park in Terre Haute, Indiana. Participants will tackle a two-lap course around Stryker Lake, featuring moderate terrain with rolling hills and stable footing. This race offers a unique opportun..

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 vibrant trail running event taking place at Willenborg Woods in Charleston, IL, on October 18, 2025. Participants can choose from various distances, including a 50K, half marathon, 10K, and 5K, catering to both competitive runners and casual nature enthusi..

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..