Trail Running calendar near Madison 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.

Event Overview The Broken Rock Trail Runs take place at Bethel Horizons in Dodgeville, Wisconsin, within the Driftless Area. The event name comes from the Broken Rock Trail, which features a steep rock-stair climb near the finish. Distances..

Run or walk on scenic trails at Fox Hill Nature Preserve to support land conservation. Choose from a 5K, 10K, or a 1-mile trail walk through forests and prairie. The event is chip-timed and benefits the Cedar Lakes Conservation Foundation.

A multi-loop trail ultramarathon in Dubuque set on a roughly 20-mile loop through the Mines of Spain Recreation Area, offering 100-mile and 100K options with substantial elevation and varied terrain.

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.

The Soul Crusher will take place in Richmond Township on Saturday 17 October 2026. You can run between 5 and 10 miles.

The Abominable Trail Race will take place in Lake Geneva on Saturday 14 November 2026. You can run between 5 and 30 kilometers.

The Frozen Assets Run will take place in Madison on Saturday 6 February 2027. You can run 5 kilometers.