Trail Running calendar near Oconomowoc 2026-2027

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 haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

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.

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..

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.

Experience a unique 5K race held entirely on the frozen surface of Lake Mendota. Participants can run walk or skate across the ice while enjoying scenic views of downtown Madison and the university campus.