Trail Running calendar near Delafield 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.

A trail running event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 10K, half marathon and 50K on rolling hills and well established trails.

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.

The Kishwauketoe Cross Country Run will take place in Williams Bay on Saturday 4 July 2026. You can run 5 kilometers.

Experience the ice age terrain of Devil's Lake at Dances with Dirt, with distances from 10K to 50 miles for every trail runner. Enjoy marked courses with aid, a famously dramatic aid station, finisher medals, and post race food and a brew.

Take on the Cliff Runner 10K on July 19, 2026 at High Cliff State Park, a rugged singletrack course with rocks, roots and steep climbs. Registration includes a Cliff Runner tee and finisher medal, with proceeds to Purdy Nature Preserve.

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 a scenic 9 mile course through Kohler Andrae State Park, with beach, boardwalk and woodland trails along Lake Michigan. Expect mostly flat terrain, unique cordwalk sections, and post race snacks in this second annual event.

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.

Run the Twisted Roots marathon or half at High Cliff State Park near Sherwood, Wisconsin. Tackle technical single track, rolling prairie and cliffside views of Lake Winnebago on scenic, community driven courses.

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.

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..