Trail Running calendar near Libertyville 2026-2027

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.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

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 diverse terrain of the historic Lemont Quarries with four trail race distances ranging from 10K to 60K. Runners navigate a mix of flat gravel paths and technical single-track trails through the woods.

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.

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.