Trail Running calendar near Oak Forest 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.

A flat, fast trail event in Lake County on crushed gravel with 50 Mile, 50K, Marathon and Half Marathon options. The Marathon is Boston qualifying, the race is cup-less, and all finishers receive medals plus post-race food and awards.

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..

Experience the Bigfoot Half Trail Run at Stoney Run County Park. This two loop course features a mix of grass, dirt trails, and gravel with manual timing and unique raffle prizes for participants.

Experience the variable terrain of the historic Lemont Quarries at this multi distance trail festival featuring laps of single track and gravel paths ranging from 10K to 60K.

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 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.

Experience a unique winter obstacle course in Lake Geneva featuring distances from 5K to 20K. Enjoy a festival atmosphere with fire pits and food trucks after conquering challenges designed for both fun and competitive athletes.

A trail event at The Forge Lemont Quarries on March 13, 2027 featuring a half and quarter marathon on wooded single and double-track trails with varied, technical terrain and one aid station for the half.