Trail Running calendar near Charleston 2026-2027

Experience the beautiful trails of Allerton Park in Monticello with a weekend of running events. Choose from a glow in the dark 5k, a 10k, or a half marathon while supporting Make A Wish Illinois.

Experience the scenic rock quarry cliffs of DePauw Nature Park in Greencastle. This event features 15k and 5k trail runs on crushed stone paths with mild grades and a few steep climbs.

A backyard ultra near Wingate, IN on a 4 mile 880 foot out and back course with gravel, grass and road sections. Runners start each loop on the hour and continue until one runner completes one more loop than all others.

A backyard ultra at Willenborg Woods near Charleston, Illinois featuring a 4.167 mile loop run each hour with a Bronze Ticket for the last finisher. Day loops use single track and groomed grass while night loops use grass trails and country..

This cross-country event offers a scenic 5K run through Lincoln Trail College, featuring a mix of grass and paved paths. A shorter Kid's Fun Run is also available on the paved course. Awards are given for overall and age group winners, and..

A 7.1 mile trail run around Lake Mingo at Kennekuk Cove County Park on June 13, 2026. The mostly trail course features hills, nine bridges, one aid station halfway and a post race party at the Hideaway Shelter.

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.

Run through a scenic reclaimed limestone quarry in Greencastle at the Vulture Vista Ultra. Choose from 6 hour or 12 hour timed events or a single 4.5 mile loop on wooded singletrack and open trails.

Quail Ridge Farm Backyard Ultra in Albion, Illinois on July 18, 2026. Registration includes a t-shirt and a ten dollar food truck voucher, camping the night before is free, and a voluntary one dollar per lap pool will be split among top fin..

A 5K trail race in Charleston, IL on July 25, 2026, featuring forest trails, about 1,100 feet of climb, a one third mile crossing of the Embarras River, a field limited to 125, and a post-race pancake and ice cream gathering.

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.

Event Overview The Howl at the Moon Ultra is a timed endurance event held at Kennekuk Road Runners in Danville, Illinois. The event features separate eight-hour and four-hour divisions for runners and walkers. Course Details Participants co..

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.

Conquer a rugged 1200 acre off road course at the Badlands Off Road Park. Choose from 5K, 10K, and 21K obstacle races featuring sand dunes and forest trails for a complete weekend of outdoor adventure.

This trail run/walk in Greenville's Patriot's Park is a 5K event supporting childhood cancer research. It takes place on scenic trails and is inspired by a personal story of courage.

Trail races at Willenborg Woods in Charleston, IL on October 16 and 17, 2026 offer distances from 5K to 100K. The course runs through timber, riverside paths, creeks and hills with full course marking and on-course support.

Experience a 5.7 mile trail race or a 2 mile nature walk along the Sangamon River at Robert Allerton Park. This community event supports local trail maintenance and features a costume contest in a scenic meadow setting.

Experience the beauty of the Illinois tallgrass prairie at Meadowbrook Park with 5K and 10K events supporting local land conservation. Runners and walkers of all ages are welcome to this annual community tradition.