Trail Running calendar near Shelbyville 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.

Oktoberfest Rotary Run is an annual fundraiser in Bloomington, Illinois, held on the third Sunday each October. The event centers at GE Park / Union Park Clubhouse (1750 GE Road) and offers a chip-timed 5K on the Constitution Trail, looping..

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..

Join the Beaver Dam Dash at Beaver Dam State Park on November 1 for scenic single track 5K, 10K and one mile fun runs to support the Macoupin Center for the Developmentally Disabled. Register early to guarantee a long sleeved tech shirt.

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..

The Schon Park 3/6/9 Endurance Runs, hosted by Ultra Bound Coaching, take place in Glen Carbon, Illinois. This timed event offers three durations: 3, 6, and 9 hours, where participants run loops on a 1.5-mile paved course featuring rolling..

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.