Trail Running calendar near Charleston 2026-2027

Join the Frozen Cock's Crow 5K at Willenborg Woods, a spirited trail run on technical singletrack with steep climbs and a stream crossing. Enjoy a family friendly, grassroots vibe and a fun post race celebration.

Trail races in Owen Putnam State Forest feature single track looped courses in 50 mile, 50K, 14 mile and 10K distances. The event is organized by the Indiana Trail Running Association and is a cupless race with limited camping.

A trail event at Hawthorn Park offering a 5 mile run, 4 mile walk and 1 mile fun run, with marked trails, volunteer support, awards and a post-race breakfast taco bar. Preregistration is required by April 12 for a shirt.

Clinton Lake Ultra on March 28, 2026 in DeWitt, IL features a 30 mile and a 10 mile trail race on three 10 mile loops, two aid stations per loop, mandatory volunteer service, race awards, and event swag.

Allerton Races on April 11 and 12, 2026 features trail and road routes, a glowing nighttime Trail Glo 5K and virtual options for every pace. Proceeds support Robert Allerton Park and Make A Wish Illinois with Wish Warrior recognition.

The The Trail Trot Cross Country 5K will take place in Robinson on Saturday 30 May 2026. You can run 3 miles.

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.

Join the Madder Than A Wet Hen 5K in Charleston IL for a rugged forest trail run featuring a knee deep river crossing and a fierce climb up Billy Goat Hill. Reward yourself after the finish with pancakes and ice cream.

A 10k trail race at Griffin Bike Park in Terre Haute on August 1, 2026. The two lap course circles Stryker Lake with rolling hills and generally stable footing; finishers earn bonus series points based on placement.

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.

Run fast rolling trails at Sand Creek in Decatur on Sept 12 and choose 4.4 or 7.6 miles for a lively trail challenge. Get a tech shirt and finisher medal while supporting the Special Operations Warrior Foundation.

Join the Miles for Marshall 5K trail run and walk on Saturday, September 26, 2026 at Patriot's Park in Greenville to support childhood cancer research and families. Run or walk scenic trails with community spirit and purpose.

Trail races at Willenborg Woods near Charleston, Illinois on October 16 and 17, 2026. Multiple distances from 5K to 100K on marked single-track trails with riverside sections, creeks, hills, volunteer support and a post race celebration.

A trail event at Robert Allerton Park in Monticello on October 25, 2026, featuring a 5.7 mile run, a 2 mile nature walk, and a virtual 5.7 mile option. A portion of proceeds supports park trail maintenance and improvements.