Trail Running calendar near Janesville 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.

Trail loops at Bethel Horizons near Dodgeville WI with three distances, varied singletrack and ridge terrain, stocked aid stations, and awards plus a tech shirt and medal.

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 Race For Open Space on Oct 11, 2026 in West Bend for a chip timed run and walk through forests, prairie and glacial moraine to benefit Cedar Lakes Conservation Foundation. Distances for all ages and awards for top finishers.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

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.

A 5k trail event in Pingree Grove, Illinois on October 23, 2026 where participants can run, walk, or ruck through a course with haunted sets, animatronics, and actors. The evening includes multiple heats plus a costume contest, bonfire, ent..