Trail Running calendar near Chicago Heights 2026-2027

Trail race in Crystal Lake, IL on October 17, 2026 offering 5 Miler and 10 Miler options on single track trails with bonus mileage. Carry your own hydration; finishers receive a race shirt and a skeleton medal.

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 looped trail event offering 50K, 25K, and a 5-mile option on mostly single-track terrain with staffed aid stations and an organizer focus on community and inclusion.

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 nighttime run and walk at Lake County Fairgrounds on October 30, 2026 featuring a timed 5K, a non-timed 2K, a market with live performances, costume contests, and awards.

A trail event at Camp Big Timber on November 8, 2026 featuring 3- and 5-mile perimeter loops plus a kids fun run. The course includes grass, gravel, a creek crossing and a post-race pancake breakfast for all participants.

A two-loop trail run at Stoney Run County Park on November 14, 2026, over mixed surfaces with on-course aid stations. Packet pick-up includes a raffle and memorabilia sales, with proceeds benefiting the park.

Late November trail festival in Lemont IL offering 10K, 20K, 30K and 60K on single and double track and gravel around historic quarries and the I&M Canal. Courses start and finish at The Forge and use lap formats.

The St. Joe Valley Happy Trail Run will take place in Roseland from Saturday 14 November 2026 to Monday 16 November 2026. You can run between 5 and 13 miles.

A Thanksgiving 5K on the Green Bay Trail at Winnetka Train Station featuring rolling start waves, a family division, packet pickup before race day, post-race refreshments, and support for local charities.

Early-season trail races at The Forge in Lemont, Illinois, on wooded single and double track trails with mud, roots and gravel. Distances offered are 13.1 miles and 6.5 miles with technical singletrack sections.

Trail races of 30k, 50k and 50 mile are scheduled March 13, 2027 at Sunset Hill Farm County Park in Valparaiso, IN, with a 16 hour time limit, one aid station, and finish awards including belt buckles and a wooden medal.

A looped trail event at Deer Grove Forest Preserve west in Palatine, IL offering 5.5 mile, 25K, 50K and 50 mile distances. The course is mostly wide and not technical with one aid station at the start and playful on course shenanigans.

A family-friendly trail event at St. Patrick's County Park offering 50k, marathon, half marathon and 10k distances with marked courses and chip timing by Watts My Time.

Flat out and back half marathon and 10 km on the limestone Great Western Trail, hosted by Fox River Trail Runners. Registration fees and donations support three local mental health charities.

Trail marathon and 10 mile on the Sag Valley Trail at Cap Sauers Nature Preserve in Palos Hills, IL, with wide horsetrail, notable elevation gain, and staffed aid stations along the routes.