Illinois
Illinois Trail Running Calendar 2026-2027
Explore the best trail runs in Illinois for 2026-2027! Our updated list features 80 exciting trail runs across the region. Find your next trail run in Illinois below and join the trail community at these great events!
October 2026
A point to point trail ultramarathon along the Hennepin Canal State Trail in Illinois, with 100 mile, 50 mile, 50K and a 100 mile relay.
Run The Woods is a trail event at Timber Pointe Outdoor Center in Hudson, IL featuring 5K and 8K races with youth divisions and a one mile untimed trail walk. Proceeds benefit Easterseals Central Illinois and Timber Pointe Outdoor Center.
Autumn Leaf Run is a 5K trail event at Oakdale Nature Preserve in Freeport on 10/03/2026. The looped course crosses prairies, creek and wooded trails and raises funds for park improvements through the Freeport Parks Foundation.
A guided two to three mile run and cemetery tour in Midlothian with a post event beer, shirt and raffle.
The Lockport Fire Foundation presents the second annual Fire Zone 5k, a community 5k run and walk on a marked loop of the Forest Preserve trail starting at Hassert Park. Registered participants present on race day receive a t shirt and finisher medal..
A 5K run and walk at College of Lake County Grayslake on October 4, 2026 raising funds for the Carrera de los Lancers Scholarship and student entrepreneurship programs.
A lap-based 24 hour endurance event at Arrowhead Lake Campground near Johnston City IL with a certified 2.07 mile gravel loop and multiple timed races.
A community 5K in Flossmoor with a parallel virtual 5K that raises funds and collects goods to support local families experiencing hidden homelessness and provide school supplies for homeless children.
Trail races on the Des Plaines River Trail in Lake County, Illinois offering half, marathon, 50K and 50 mile distances on a flat crushed gravel course.
A multi-distance trail running event at Farmdale Reservoir near East Peoria featuring single-track trails, aid stations, camping, and awards for finishers.
A 5K walk and run on October 10 supporting men's mental health with an in person course in New Lenox and a virtual 5K option.
Two day trail running event at Willenborg Woods in Charleston IL with distances from 5K to 100K on single track trails, riverside paths and hilly terrain.
Trail run at Saw Wee Kee Park on October 17, 2026, over soft, twisting trails with variable footing. Bib-timed waves, part of a four-race series with collectible medal pieces and seasonal swag.
Nature-based out-and-back event in Roscoe, IL offering a 5K run or 2 mile walk on mixed gravel and crushed limestone, starting at Roscoe Middle School and passing a water station twice.
Trail event in Crystal Lake offering 5 and 10 mile looped courses on single-track forest trails, with a race shirt and skeleton finisher medal.
A 5K and 10K trail run and walk through Swallow Cliff South in Palos Park on October 17, 2026, with gravel trails, elevation changes, reusable race cups, and age group awards.
A fall race at Richardson Adventure Farm in Spring Grove featuring 10K, two 5K options and a 1 mile family run through the corn maze with finisher medals for all.
A chip timed 5K and an untimed 1 mile fun walk at GE Park in Bloomington on October 18, 2026, raising funds for BN Sunrise Rotary Youth Services and the CCHS Rotaract Club. Awards include ceramic steins for top 5K age group finishers.
A nighttime 5K trail run in Pingree Grove Illinois with ghostly actors and animatronics, plus a postrace DJ, contests, food, and a finisher medal and event t shirt.
A grassroots trail ultra at Deer Grove Forest Preserve on a 5.5 mile loop with 25K and 50K options, marked course, staffed aid stations, and prize money for top finishers.