Trail Running Calendar Illinois 2026-2027

A point to point, all-trail ultramarathon along the Hennepin Canal State Trail in Illinois offering 100 mile, 100 mile team relay, 50 mile and 50K options, with aid stations every 3 to 7 miles and a 30 hour cutoff for Western States eligibi..

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.

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 fini..

A coffee-themed fun run on October 4, 2026 at Case Creek Trails in Coal Valley, IL offering 2K and 5K routes, hot drinks after the course, optional swag, and proceeds supporting QC PAWS.

A multi-format endurance event at Arrowhead Lake Campground in Johnston City, IL, run on a certified 2.07 mile loop. Multiple timed races are offered with on-course aid, finisher medals and awards, camping, and chip timing provided.

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.

Multiple endurance trail distances on a flat, crushed gravel section of the Des Plaines River Trail, starting and finishing at Half Day Forest Preserve in Lake County, Illinois. The marathon is a Boston Qualifier and the event runs each Oct..

A multi-distance trail event at Farmdale Reservoir near East Peoria, IL on October 10-11, 2026, featuring races from 10K to 100 miles, single-track and prairie trails, on-site camping, aid stations, and awards for finishers.

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.

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.

A memorial 5K run and 2 mile walk in Roscoe, Illinois on October 17, 2026. The out and back course uses local trails and crushed limestone, includes a water station, and offers a virtual supporter option.

October 17, 2026. A trail race in Crystal Lake, IL with 5 mile and 10 mile options on single-track trails through Veteran Acres and Sternes Woods, cup-less aid, and a 3 hour 30 minute cutoff.

A fall event at Richardson Adventure Farm in Spring Grove, IL featuring 5K and 10K courses through the corn maze and farm, a family 1-mile run for children, and a kids 100m dash with ribbons for finishers.

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 Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.

A trail ultramarathon at Red Gate Woods near Chicago offering 25K and 50K on a clockwise single track loop of about 5.5 miles, with staffed aid stations, course maps, and no pacers allowed.

Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.

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.