Trail Running calendar near Charleston 2025-2026

Run the Kennekuk Road Runners Siberian Express, a 7.45 mile winter trail through Kickapoo State Park with steep climbs, creek crossings and wildlife. First 150 finishers receive awards and post race festivities are at Vermilion Brewing.

Take on the Frozen Cock's Crow 5K, a wintry route through rugged, steep trails at Willenborg Woods near Charleston, Illinois. Expect technical climbs, friendly trail support and a warm post race celebration to reward your effort.

OPSF 50|50 is a trail running weekend in Owen Putnam State Forest near Poland, offering 50M, 50K, 14 mile and 10K on a rolling, technical 14 mile loop. This cupless event requires runners to carry 20 oz of water and awards finisher medals.

Run scenic single track loops around Clinton Lake near DeWitt, IL through forests, hills and meadows with a bridge connecting the course. Choose the 30 Miler or 10 Mile, enjoy post race food and a long sleeved finisher item.

Enjoy scenic road and trail courses at Allerton Races in Monticello with a Half Marathon, 10K and a nighttime Trail Glo 5K. Proceeds benefit Robert Allerton Park and Make A Wish Illinois, and virtual options are available.

The Lake Mingo Trail Run will take place in Danville on Saturday 13 June 2026. You can run 7 miles.

Take on Madder Than A Wet Hen, a rugged 5K trail race at Willenborg Woods in Charleston on July 25, 2026, with river crossings, steep climbs and roughly 1,100 feet of gain. Field limited to 125, with post race pancakes and ice cream.

Run a scenic 10k around Stryker Lake at Griffin Bike Park with rolling hills, wide trails and two friendly laps that make passing easy. Camping at Fowler Park and the concurrent DINO Gravel Triathlon create a lively event atmosphere.

Hit the Wild Wild Wilderness at Kickapoo State Recreation Area on September 12, 2026 with 5K or a rugged 7.45 mile trail through woods, steep climbs and creek crossings. Celebrate finishes with food, drinks and awards.

Hit the fast rolling Sand Creek trails near Decatur with 4.4 or 7.6 mile options, in person or virtual. Enjoy a technical long sleeve shirt, finisher medal and snacks while supporting the Special Operations Warrior Foundation.

Join the Miles for Marshall 5K trail run and walk at Patriot's Park in Greenville to support childhood cancer efforts. Enjoy scenic trails, community spirit, and a meaningful cause this September 26, 2026.

Shake Your Trail Feather Trail Run (Oct 16 to 17, 2026) invites runners to explore single track trails, creeks and hills in Willenborg Woods, with distances 5K to 100K. Finishers can join a community celebration and enjoy on course support.

Join Allerton Park Trail Run on Oct 25, 2026 for a scenic 5.7 mile route along the Sangamon River, a relaxed 2 mile nature walk, or a virtual 5.7 mile option. Expect roots and sharp turns and know proceeds help fund park improvements.