Trail Running calendar near Chicago 2026-2027

Join this community run and walk at Vollmer Road Grove Forest Preserve to support homeless school children. Participate in person on the paved 5K trail or join virtually to help provide essential school supplies for families in need.

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..

Experience a natural trail run at Saw Wee Kee Park featuring a soft path with twists and turns. Complete this event to earn a piece of the 2026 series medal and enjoy seasonal swag in a beautiful outdoor setting.

Timed trail races of 24, 12 and 6 hours take place on the dirt and grass loops of St. Patrick's County Park in South Bend. The course has three short asphalt crossings and proceeds benefit the ALS community.

Trail races of about 5 and 10 miles through Veteran Acres and Sternes Woods in Crystal Lake, IL, with single-track trails, a cupless course, packet pickup options, and finisher medals for all distances.

Experience a haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

A woodland ultra with 50K, 25K and 5-mile options run on a 5.5-mile single-track loop at Deer Grove Forest Preserve, featuring multiple stocked aid stations and explicit inclusion policies for race entries.

Celebrate Halloween and support animal shelters at this dog friendly 5k in Busse Woods. Enjoy a flat paved course with treats for both humans and leashed pets at the finish line.

A Halloween night run and walk through the Lake County Fairgrounds. The event includes a timed 5K and a non-timed 2K walk, costume prizes, and entry to a festive market. Bring a flashlight for the evening course.

Embrace an autumn adventure at the Big Timber XC Challenge, a trail run featuring a famous creek crossing through the woods of Camp Big Timber. Choose between a 3-mile or 5-mile course on grass and gravel paths. All runners get a shirt and..

A half trail run at Stoney Run County Park on November 14, 2026, held over two loops across grass, pavement, gravel and single-track trails, with aid stations, on-site packet pick-up, a raffle and informal timing using popsicle-stick finish..

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.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

A trail based Turkey Trot at Southwestern Michigan College offering 10K, 5K and a free 1K kids run, chip timed with live results, guaranteed tech shirts for early registrants and age division medals.

A dog friendly trail running event at Lake Geneva Ziplines and Adventures with a 4 mile loop, an 8 mile option, and a focus on Canicross. Awards are reserved for teams running with dogs and all finishers receive a small gift.

A winter obstacle event in Lake Geneva on January 30, 2027 offering distances from a kids course to a 20K Yeti Challenge, plus a competitive Elite division with cash prizes, team entries, and a virtual race option.

Woodsy single track races in March 2027 at Soldiers Memorial Park, LaPorte, IN. Distances are a 10K and a half marathon over winding, not flat trails; aid stations are about every 2.5 miles and the event is cupless.

Trail races at The Forge take runners through wooded single and double track trails around the Lemont Quarries. The event offers a trail half and a quarter marathon with variable terrain, one aid station for the half, and chip timed results..