Trail Running calendar near Oakwood 2025-2026

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..

Madder Than a Wet Hen is a 5K running event held in Charleston, Illinois, at 17737 E County Road 380N. The race offers participants a scenic course through the local area, providing a community-focused atmosphere ideal for runners of all levels. The event takes place in July, promising summer weathe..

The Dino-Griffin 10K Bonus Run is a trail running event held at Griffin Bike Park in Terre Haute, Indiana. The race features a 10-kilometer course consisting of two laps around Stryker Lake, with moderate terrain, rolling hills, and generally stable footing. The wide trails allow for easy passing an..

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, held at Willenborg Woods in Charleston, Illinois, offers a scenic and challenging trail running experience. Participants can choose from distances including a 50K ultra, half marathon, 10K, and 5K. The course features single-track trails winding through pristi..

The Allerton Park Trail Run, organized by the Second Wind Running Club, takes place at Robert Allerton Park in Monticello, Illinois. The event features a challenging 5.7-mile trail run along scenic river trails with roots, ruts, and sharp turns, and a 2-mile nature walk. Participants can enjoy a fes..

The OPSF 50/50 Trail Race is a well-established running event held in Owen-Putnam State Forest near Poland, Indiana, about an hour from Indianapolis. Organized by the Indiana Trail Running Association, it offers multiple distances: a 50-mile ultra, a 50K, a 14-mile run, and a 10K trail race. The cou..