Trail Running calendar near Charleston 2025-2026

Join the 27th annual Rattlesnake Master Run for the Prairie in Urbana, Illinois to support Grand Prairie Friends with 5K and 10K trail and park courses plus virtual options. Expect medals, music, and a celebration of local prairies.

Run a scenic wooded 5K loop at Ballard Nature Center on November 16, 2025, choosing a one lap 5K or the 4 Hour endurance challenge to rack up as many laps as you can. Try the Oscar Mike Ruck SACK for weighted ruck awards and a finisher meda..

Start 2026 at the Siberian Express, a 7.45 mile winter trail run at Kickapoo State Recreation Area on January 3. Expect steep climbs and creek crossings, carry your own hydration, and warm up at a friendly post race gathering.

Run the Frozen Cock's Crow 5K in Willenborg Woods on Feb 14, 2026, a rugged winter trail with steep climbs, a stream crossing and scenic singletrack. Join the trail community afterward for food, fun and warmth.

OPSF5050 in Owen Putnam State Forest near Poland IN offers 50 mile, 50K, 14 mile and 10K trail races. Enjoy mostly singletrack, rolling hills and technical terrain on a scenic lollipop loop and remember this cupless event requires carrying..

Test your limits at the Grind on the Grid Backyard Ultra in Wingate, IN, where runners repeat a roughly 4.17 mile out and back loop every hour until one person remains. Tents and canopies are welcome the night before and the field is limite..

Challenge yourself in 6 hour or 12 hour relays and ultras on a scenic loop of trails and roads at Hawthorn Park. Solo and team entries, camping, on site food and finisher medals make it a festive weekend of racing.

Push your limits at Elsa Chicken Plucker Backyard Ultra in Willenborg Woods, Charleston IL where runners run a 4.167 mile loop every hour until one remains. Enjoy trails and compete for a Bronze Ticket to the Big Dog's World Championship.

Join the 28th annual Lake Mingo Trail Run on June 6, 2026 in Danville, IL for a scenic 7.1 mile loop of trails, hills and marshes where mud and wildlife add to the fun. Celebrate with food and beer at the post race party.

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 the rugged Wild Wild Wilderness at Kickapoo State Recreation Area with a scenic 7.45 mile trail or 5K option. Expect steep climbs, creek crossings, awards at the finish and the chance to complete the Grand Slam.

Shake Your Trail Feather runs October 16 and 17, 2026 at Willenborg Woods in Charleston, IL, with distances from 100K to 5K on winding single track, creek crossings and riverside paths. Friendly trail support and a post race celebration awa..