Trail Running calendar near Sheboygan 2025-2026

Take on the Whitewalker Ultra 100k in Palmyra WI, a two loop 100k over scenic Ice Age Trail and Scuppernong trails. Expect rugged single track, aid stations on course, and a 24 hour finish limit for a true winter challenge.

Trailbreaker in Waukesha invites runners to scenic courses along Glacial Drumlin and Fox River trails, with distances from marathon to Kids 1K. New ruck events add variety while proceeds support local parks and the urban forest.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Tackle the scenic Northern Kettle Moraine on a point to point trail run through rolling ski trails, rocky singletrack and the forest high point. Choose 50K or 25K with shuttle service, aid stations and post run food at Greenbush Group Camp.

Join Moonlight Meltdown and Sunset Safari in Belgium, Wisconsin for a flat, well lit 5k or a scenic 10k into Harrington Beach State Park. Chip timing, shirts and refreshments raise funds for Belgium Fire and Rescue and local youth programs.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Tackle an off road cross country 5K through scenic trails at PM Conservation Park on Sunday, May 17. Open to runners and walkers of all ages, dogs welcome and strollers not recommended.

Join the 17th annual Crossroads Trail Run & Walk at Big Creek Nature Preserve in Door County for scenic 2K, 5K and 10K courses. All participants receive a native tree and post race snacks while supporting conservation and outdoor education.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Tackle a rugged 10K through High Cliff State Park's single track trails of rocks, roots and steep climbs for an unforgettable challenge. Finishers receive a Cliff Runner shirt and medal and proceeds support the Purdy Nature Preserve.

Join the 9th Annual Jazz Blueberry Trail Run and Walk at Jazz Blueberry Farm in Shelby on Sunday, July 26 for scenic trails and 5K, 10K and 1 mile fun run options. Expect farm views, family fun and blueberry swag.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Thanks Sandy is a 9 mile trail run through Kohler Andrae State Park, blending beach stretches, pine and prairie trails with a memorable cordwalk. Presented by TYDISH Running, this second annual event serves coastal views, varied terrain, an..

Experience a spirited trail running weekend with 50 mile and 50K ultras plus marathon and half marathon options, famed for huge finisher medals and a lively post race party. Registration for 2026 is closed but a wait list will open soon.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Run scenic single track and rolling prairies at Twisted Roots on Sunday, September 20, 2026 at High Cliff State Park, WI, with marathon and half marathon distances. Expect technical trails, lake views, friendly aid stations and a post race..

Enjoy a scenic fall run, walk and roll through 125 acres of wooded trails, meadows and ponds. Choose a half marathon, 5K, 5K ruck or family one mile loop and support Zachariah's Acres for children with special needs.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Celebrate pups and fitness at Paws for a Cause in Denmark WI on Oct 17 2026, with canicross and solo trail runs at several distances. Costume contests, Paw Parazzi photos, vendors and food benefit Crisis Cafe.