Trail Running calendar near Charleston 2026-2027

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 in Albion, Illinois on July 18, 2026 with a registration fee that includes a t-shirt and a ten dollar food truck voucher. Free camping is available the night before and a voluntary per-lap pot funds top prizes.

A summertime 5K at Willenborg Woods near Charleston, IL featuring winding forest trails, a one third mile crossing of the Embarras River and a steep finish at Billy Goat Hill. The field is limited to 125 runners with a post race pancake and..

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 cross-country 5K on the Lake Land College campus in Mattoon, Illinois, featuring rolling hills, grassy fields and wooded paths. The event highlights the college's second-year cross country program and includes packet pickup at the Field H..

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, mostly flat 2 mile obstacle course at Richland Community College on September 19, 2026, raising funds for the Student Veterans' Resource Center with 20 to 25 obstacles and finisher rewards.

Midwest Spartan Trifecta Weekend at Badlands in Attica IN offers Sprint, Super and Beast obstacle races across 1,200 acres of sand dunes, rocky paths, forests and creek beds; kids races and spectator options are also available.

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.

Trail races at Willenborg Woods in Charleston, Illinois on October 16 and 17, 2026 offer distances from 5K to 100K on single track trails with creek crossings and technical sections.

A fall event at Allerton Park featuring a 5.7 mile trail run, a 2 mile nature walk, and a virtual 5.7 mile option. The riverside course has roots, ruts, and sharp turns, with awards, costume prizes, and park donations.

A community road-and-trail event at Meadowbrook Park in Urbana supporting Grand Prairie Friends, offering 5K and 10K runs, a 5K walk, plus virtual options, medals, and t-shirts.

Trail races in Owen-Putnam State Forest with 50 mile, 50K, 14 mile and 10K options on a mostly single track lollipop course. Aid stations are cupless and runners must carry 20 oz of water.

Backyard Ultra in Wingate IN on April 17 2027 featuring repeated 4 miles 880 feet loops over road gravel and grass. Each loop starts every hour and the last runner to finish a loop is the winner.