Trail Running calendar near Rolling Meadows 2026-2027

Experience natural dirt trails and scenic views at this Janesville event featuring a competitive 5k run and casual walk. Stay for the heritage celebration with food trucks and live music after you finish.

Run or walk along the tree lined Oak Leaf Trail before finishing at the Oktoberfest celebration in Glendale. This event features a 5k run and a 54 yard dash with post race refreshments and festival entry.

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.

Experience a fast and flat crushed gravel trail through the forests and wetlands of Lake County. Featuring four distances from a half marathon to a 50 mile ultra, these races offer a scenic out and back course perfect for personal bests.

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.

Take on the Soul Crusher trail run through the forested paths of Veteran Acres & Sternes Woods in Crystal Lake. The event features a 5-mile loop course with a chance for extra mileage, finishing with a unique skeleton medal. Prepare for a c..

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.

Fancy Nonsense 25k/50k The Fancy Nonsense 25k/50k is described as a nonsensical running experience born from mischief and imagination, designed to provide a space for the joy of running. The event takes place in the Palos Trail System at Re..

The Howl-o-ween 5k - Schaumburg will take place in Rolling Meadows on Saturday 24 October 2026. You can run 5 kilometers.

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.

The Abominable Trail Race offers trail distances from 5K to 30K at LG Ziplines and Adventures. Run solo or form a relay team for the 30K. The event includes a festival base camp with music, food, and vendors.

Misty's Legacy is a virtual 100-mile challenge supporting the preservation of the historic Beebe Ranch. Participants walk, run, ride, or cycle at their own pace, tracking progress for a commemorative medal. The event is open to all and oper..