Trail Running calendar near Middleton 2026-2027

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.

Trail races at Mines of Spain near Dubuque include 4 mile, 7 mile and half marathon distances on varied singletrack and prairie trails, with aid stations, cup free practices, shuttle service and age group awards.

A multi-format trail running event at Blackhawk Ski Club in Middleton WI on August 22, 2026, offering solo 3/6/12 hour challenges, team relays, and a 1.7 mile fun run on mixed grass and single-track with notable hill features.

Echo 136 is a 136 mile trail event on the Ice Age State Trail in the Southern Kettle Moraine, featuring varied trail surfaces, nine staffed aid stations and a 55 hour time limit.

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.

Run or walk the Fall into Fall Trail 5k in Janesville on October 3, a scenic timed trail through wooded dirt paths with beautiful fall views. Stay for live music, food trucks, beer and wine tasting and raffles; register by Sept 15 to guaran..

A multi-distance trail event at Mirror Lake State Park on October 3, 2026, with a kids mile, 5K, 10K and half marathon; chip-timed races, cupless aid, park trail terrain and post-race s'mores while raising funds for park projects.

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.

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 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.

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.