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, IL on Jul 18, 2026 with a registration fee that includes a t-shirt and a $10 food truck voucher. Camping is available the night before and a voluntary $1 per lap pool will be split among top finishers.

A summertime 5K trail race in Charleston, Illinois on July 25, 2026 featuring about 1,100 feet of climb, a one third mile river crossing, a steep finish on Billy Goat Hill, and a field limited to 125 runners.

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 running event at Willenborg Woods in Charleston IL offering 100K, 50K, 16 miler, 8 miler and 5K on marked single track through timber, riverside paths and creek crossings. Pets are not allowed.

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 of 50 miles, 50K, 14 miles and 10K take place on a mostly single track lollipop course in Owen-Putnam State Forest. The event is cupless so runners must carry water and aid stations do not provide cups.

A backyard ultra in Wingate, Indiana, run on a 4 miles 880 feet loop with mixed surfaces. Loops start every hour and the last runner to complete a loop is declared the winner.