Trail Running calendar near Charleston 2026-2027

A backyard ultra in Wingate, IN on a 4 miles 880 feet out and back course with mixed gravel, grass, and road surfaces. Loops start one hour apart, each must be completed within the hour, and the last person to finish a loop wins.

A Second Wind Running Club event on May 9, 2026, the Buffalo Trace Trail Race follows an approximately 5-mile course through woods and prairie at Lake of the Woods; registration is available online and proceeds benefit the Forest Preserve F..

A time based endurance event on a scenic 5K loop offering six hour and twelve hour formats for solo runners, teams, and walkers, with Runners Village, optional camping, live tracking, and post race awards.

A 3.1 mile trail race through wooded routes at the Vigo County Conservation Club in Terre Haute, Indiana. Registration runs from April 1 to May 23 and the entry fee is $30.

A Backyard Ultra at Willenborg Woods in Charleston, IL on May 30, 2026 where runners repeat a 4.167 mile trail loop each hour until one finisher earns a Bronze Ticket toward the Big Dog's Backyard Ultra World Championship.

A 3.1 mile cross country 5K across grass and paved paths on the Lincoln Trail College campus, plus a one mile Kid's Fun Run around the pond. Age group medals and overall prizes are listed for the 5K.

A 7.1 mile trail loop around Lake Mingo at Kennekuk Cove County Park featuring mostly trail surface, hills, nine bridges, one midway aid station, and finisher medals for the first 150 finishers; a post-race party follows.

A family-friendly adventure trail 5k at Griffin Bike Park with obstacles like a floating bridge, race tee and timing chip included, team rebate options, age-group awards and participant rules on strollers, bikes and children.

A runner-built 4.5 mile loop ultra in a reclaimed limestone quarry offering 6 and 12 hour solo or relay options plus a single 4.5 mile trail run, two aid stations with Tailwind, and support for local youth track programs.

A Backyard Ultra at Quail Ridge Farm in Albion, Illinois on July 18, 2026. Registration includes a t shirt and a ten dollar food truck voucher, with free camping available the night before.

A summer **5K** at Willenborg Woods in Charleston, IL featuring winding forest trails, a one third mile river crossing through the Embarras River, a steep finish climb called Billy Goat Hill, and a small field limited to 125 participants.

A two lap 10 km trail run around Stryker Lake at Griffin Bike Park on August 1, 2026 with rolling hills, generally stable footing, onsite registration, and series bonus points for finishers.

Experience a trail run through Forest Park on the General Dacey Trail in Shelbyville. Participate in a 5K or 1 mile race featuring team competitions, post race refreshments, and a gathering at the local aquatic center.

A loop ultrarunning event at Kennekuk Cove County Park with 3.25 mile laps, aid stations, camping, shirts and swag bags, and four hour and eight hour runner and walker options. Field limited to 250 participants.

Experience the 46th annual trail run through Kickapoo State Recreation Area featuring a scenic pond loop and a longer 95 percent trail course with creek crossings and steep hills.

Experience fast rolling terrain at the Sand Creek Trail Run in Decatur. Choose between 4.4 and 7.6 mile distances to support the Special Operations Warrior Foundation through the scenic Macon County Conservation District.

A timed two mile obstacle course at Richland Community College on September 19, 2026 that raises funds for the Student Veterans' Resource Center. The event features 20 to 25 obstacles, awards for top finishers, and volunteer and gift regist..

A weekend of obstacle-course racing at Badlands Off Road in Attica, IN offering Sprint, Super, Beast and kids distances across rugged sand, rock, forest and creek terrain.

A 5K trail run or walk at Patriot's Park in Greenville on 09/26/2026 focused on community support for children and families affected by childhood cancer, with registration open 03/02/2026 and a $35 fee.

A multi-distance trail event at Willenborg Woods in Charleston, IL offering 5K to 100K options on marked single-track trails with technical sections, on-course support, and a post-race celebration; pets are not allowed.