Trail Running calendar near Oakwood 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.

Join the 28th annual Lake Mingo Trail Run on June 13, 2026 at Kennekuk Cove County Park, a scenic 7.1 mile loop mostly on natural trails with rolling hills and nine bridges. Celebrate afterward with food, beer, and great trail camaraderie.

Take on a rugged 5K at Willenborg Woods in Charleston with winding trails, a one third mile river crossing and about 1,100 feet of climbing up Billy Goat Hill. Field is limited to 125 and finishers get 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.

Hit the trails at Run The Woods on October 3, 2026 in Hudson IL with 5K and 8K races, youth divisions, and a one mile trail walk for all ages. Proceeds support Easterseals Central Illinois and Timber Pointe Outdoor Center.

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.

Enjoy the Allerton Park Trail Run on October 25, 2026 at Robert Allerton Park in Monticello Illinois, featuring a scenic 5.7 mile riverside trail, a relaxed 2 mile nature walk, and a virtual option. Proceeds support park upkeep and the day..