Trail Running calendar near Charleston 2025-2026

The Quail Ridge Farm Backyard Ultra will take place in Albion on Saturday 19 July 2025.

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, characterized by moderate terrain with rolling hills and generally stable footing. The wide trails allow for..

The Wild Wild Wilderness is an annual running event held at Kickapoo State Recreation Area in Oakwood, Illinois. Established in 1981, the race features multiple distances including a 5K, a challenging 7.45-mile trail run, and a combined WWW Challenge. The 7.45-mile course is predominantly trail-base..

The Shake Your Trail Feather Trail Run takes place at Willenborg Woods in Charleston, Illinois, offering a variety of distances including 5K, 8-mile, 16-mile, and 50K ultra runs. Set amidst pristine timber, grassy riverside paths, and babbling creeks, the course features technical single-track trail..

The Allerton Park Trail Run, held at Robert Allerton Park and Retreat Center in Monticello, Illinois, features a challenging 5.7-mile trail run and a 2-mile nature walk. The course follows the Sangamon River and includes natural obstacles like hidden roots, ruts, and sharp turns, offering a rugged t..

The OPSF 50/50 Trail Race is a well-established running event held in Owen-Putnam State Forest near Poland, Indiana. Organized by the Indiana Trail Running Association, it offers multiple distances including a 50-mile ultra, 50K, 14-mile, and 10K trail races. The course features mostly single-track..

The Hawthorn Half Day Relay & Ultra, held in Terre Haute, Indiana, is a unique endurance event established in 2006, celebrating its 20th anniversary in 2026. Participants can choose between 6-hour or 12-hour races on a scenic 5K loop combining trail and road, with a shorter ½-mile course available n..

The Elsa Chicken Plucker Backyard Ultra is a unique trail running event held at Willenborg Woods in Charleston, Illinois, featuring a 4.167-mile loop that runners complete every hour. Set on 149 acres of scenic trails, the course includes single-track paths, groomed grass trails, riverside views, ri..