Trail Running calendar near Charleston 2025-2026

Shake Your Trail Feather at Willenborg Woods in Charleston IL on Oct 18, 2025. Choose from 5K, 8 mile, 16 mile or 50K on scenic single track through timber, creeks and riverbanks with a friendly, grassroots finish line vibe.

The Allerton Park Trail Run, hosted by Second Wind Running Club, takes place at Robert Allerton Park and Retreat Center in Monticello, Illinois. The event features a challenging 5.7-mile trail run along the Sangamon River, known for its hid..

Rattlesnake Master Run for the Prairie is a community running event in Urbana, Illinois, at Meadowbrook Park. The 27th annual edition features a 10K Run, a 5K Run, and a 5K Walk, plus 5K and 10K Virtual Races for remote participants. The co..

On the Move for Men's Health 4-Hour Endurance Challenge takes place at Ballard Nature Center in Altamont, Illinois, on a 5K wooded trail loop with rolling hills. Runners aim to complete as many laps as possible in four hours, with breaks in..

Set in Kickapoo State Recreation Area, Oakwood, Illinois, the Siberian Express Trail Race is a 7.45-mile, 95% trail course that winds east from the park into woodlands, featuring steep hills, creek crossings, and wildlife sightings. The eve..

Event OPSF5050 is a trail running event held in Owen-Putnam State Forest near Poland, IN (4850 Fishcreek Rd). Distances offered include: 50 miles 50 km 14 miles 10 km trail The event is organized by the Indiana Trail Running Association (..

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 combin..

Test your limits at Elsa Chicken Plucker Backyard Ultra in Willenborg Woods with an hourly loop through single track, grass trails and the Tunnel of Trees. Bronze Ticket can send you toward the Big Dog World Championship.