Trail Running calendar near Sheboygan 2026-2027

Celebrate the season with a 5K run through the scenic trails of Brown County Reforestation Camp. Finishers get a bottle of local maple syrup, and a pancake breakfast is included. The event also features a family-friendly fun run and support..

Trailbreaker in Waukesha on March 29, 2026 offers marathon, half, 10K, 5K, walk, ruck events, a Kiddos 1K, and The RAD, with proceeds supporting the Park Foundation and courses on local trails including the Glacial Drumlin.

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 point to point trail run on the Northern Kettle Moraine Ice Age Trail near Greenbush, WI. Offers 25K and 50K distances with transportation to starts, aid stations, and a finish area with food and shelter.

Three chip timed races in Belgium, WI on April 25, 2026: a flat moonlit 5k road course, a 10k hybrid with a trail section through Harrington Beach State Park, and a Lakeview half marathon with lake and rural scenery.

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 event in Delafield, Wisconsin offering half marathon, 10K, 5K, ruck options and a Kiddos 1K; proceeds benefit Tall Pines Conservancy and courses use marked park trails.

Pere Marquette XC 5k at PM Conservation Park in Ludington on May 17 invites runners and walkers of all ages to a scenic off road 5k. Dogs are welcome and top finishers earn awards across age groups.

This 17th annual trail run offers 2K, 5K, and 10K distances through the Crossroads at Big Creek Nature Preserve. Participants receive a native tree and post-race snacks, with all proceeds supporting environmental education.

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 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.

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 5K, 10K, and 1-mile fun run take place at Jazz Blueberry Farm on July 26, 2026, over cross country style trails. Pre-registration includes guaranteed shirts for full price entries and awards are given to top age group 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.

Run along Lake Michigan's shoreline in this evening 9-mile trail event at Kohler-Andrae State Park. The course features sand, boardwalks, and forest trails under the sunset. Stay afterwards for snacks and celebration by the beach.

Trail races on August 29 and 30, 2026 offering 50 Mile, 50K, 26.2 Mile and 13.1 Mile distances. Registration is closed and a wait list will be available; organizers state the race includes notably large finisher medals.

Trail races at High Cliff State Park featuring full and half marathon distances on single track, prairie and cliffside terrain with a cupless event policy and postrace pasta buffet.

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 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.

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.