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..

Miles for Marshall 5K Trail Run for Childhood Cancer is held in Greenville, Illinois, at 1000 Patriot's Park, on Saturday, September 27, 2025. The event features a 5K Run/Walk along a scenic trail course suitable for runners of all levels. Described as an extraordinary, heartwarming adventure, it bl..

Shake Your Trail Feather Trail Run takes place at Willenborg Woods in Charleston, Illinois, offering four distances: 50K, 16-mile, 8-mile, and 5K to suit a range of trail runners. The course uses true trail terrain with single-track paths through timber, grassy riverside segments, creeks, and hills,..

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 hidden roots, ruts, and sharp turns, as well as a 2-mile nature..

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 course circles Meadowbrook Park’s 130-acre prairie and include..

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 the Trail Village. The race offers special divisions for we..

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 event emphasizes a wintry Midwest experience, with a time limit..

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 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..

Elsa Chicken Plucker Backyard Ultra is a Bronze Ticket Event held at Willenborg Woods in Charleston, Illinois, on 149 acres of lovingly maintained trails. Runners tackle a 4.167-mile loop every hour, with the last athlete standing earning a Bronze Ticket toward Big Dog’s Backyard Ultra World Champio..