Trail Running calendar near Glendale 2026-2027

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.

Run or walk through the beautiful Fox Hill Nature Preserve this fall. Choose from trail runs, a walk, or a kids' race, all supporting local land conservation. Experience deciduous forests, restored prairies, and scenic glacial moraines.

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 seasonal 5k trail run in Pingree Grove featuring haunted sets and live actors. Enjoy a post race bonfire, costume contest, and live entertainment after your run.

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 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.

Experience a unique winter run or skate entirely on the frozen surface of Lake Mendota. The 5K course starts and ends at The Edgewater, offering views of Madison's skyline and university campus. Choose from timed running, untimed walking, o..

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..