Trail Running calendar near Libertyville 2026-2027

A technical trail event at Franklin Creek State Natural Area near Franklin Grove, IL, offering 5K and 10K courses with multiple creek crossings, notable elevation changes, on-course water at key points, race shirts, and awards.

The Naperville Trails Half Marathon & 10K is set for September 5, 2026 in Wheaton, Illinois. Runners can choose from half marathon and 10K distances, with virtual options also available.

Course and Terrain The Echo 136 is a 136-mile ultramarathon that uses the Ice Age State Trail. The course travels north from the Southern Unit of the Kettle Moraine State Forest near Whitewater, Wisconsin. The terrain includes wide groomed..

Event Overview The Wisconsin Trail Series is a trail running and walking event series held from April to October in 2026. It consists of seven individual races held monthly, culminating in a series finale. The events take place in Oconomowo..

Explore a multi-loop trail course at Tryon Farm in Michigan City. The 50k runs on a 4-mile loop featuring fields, dirt trails, and minimal pavement. Proceeds support the Tryon Farm Institute.

Run or walk the Fall into Fall Trail 5k in Janesville on October 3, a scenic timed trail through wooded dirt paths with beautiful fall views. Stay for live music, food trucks, beer and wine tasting and raffles; register by Sept 15 to guaran..

A fall event at Zachariah's Acres in Oconomowoc that raises funds for children with special needs. Routes include a half marathon, two 5K options including ruck, and a one mile family walk and roll through prairie and woodland scenery.

A flat, fast trail event at Half Day Forest Preserve offering Half Marathon, Marathon, 50K and 50 Mile distances on crushed gravel through forests and wetlands with aid stations, finisher medals and the Marathon as a Boston qualifier.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

Event Overview The Wisconsin Trail Series is a trail running and walking event series held from April to October in 2026. It consists of seven individual races held monthly, culminating in a series finale. The events take place in Oconomowo..

A 5k trail event in Pingree Grove that combines haunted sets, animatronics, and actors with multiple 5k heats; the day also features a costume contest, bonfire, live entertainment and food options.

Trail ultraruns of 25K and 50K on a 5.5 mile loop at Red Gate Woods near Willow Springs. Mostly single track with staffed aid stations and a 5pm cutoff; no pacers allowed.

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..

The Bigfoot Half Trail Run takes place on a mixed-terrain course in Stoney Run County Park. This event features an on-course raffle, old-school timing with popsicle sticks, and a unique Bigfoot hat for participants. Aid stations are availab..

A trail race at The Forge in Lemont, IL on November 14, 2026 offering 10K, 20K, 30K and 60K on single and double track trails with variable surfaces, an aid station for multi-lap races, and a 400-runner cap.