Trail Running calendar near Charleston 2025-2026

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 and a challenging 7.45-mile trail run that covers steep hills, creek crossings, and scenic woodland terrain. The c..

The Shake Your Trail Feather Trail Run takes place at Willenborg Woods in Charleston, Illinois, offering a variety of distances including a 50K ultra, half marathon (16 miles), 10K, 8-mile, and 5K races. Set amidst scenic timber, riverside paths, creeks, and hills, the course features technical sing..

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

The OPSF 50/50 Trail Race is a well-established 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 course feat..

The Hawthorn Half Day will take place in Terre Haute on Saturday 23 May 2026. You can run between 6 and 12 kilometers.

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 riverside views, ridge-top challenges, single-track paths, gr..