Trail Running calendar near Sheboygan 2026-2027

Event Overview The HELP in Motion Trail Run takes place from October 1 to 31, 2026. The event raises awareness about domestic violence, honors lives lost, and supports survivors. Event Details Participants can choose from an in-person trail..

Tackle a 1.5-mile farm-themed obstacle course at Heim's Hillcrest Dairy. The event features challenges like feeding calves, flipping tires, and climbing hay bales. Afterwards, enjoy a yogurt bar and an optional farm tour.

Run or walk along the tree lined Oak Leaf Trail before finishing at the Oktoberfest celebration in Glendale. This event features a 5k run and a 54 yard dash with post race refreshments and festival entry.

Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.

Test your endurance at the inaugural HELIOS Ultra in the Southern Kettle Moraine Forest. Choose between 6, 12, or 20 hour timeframes as a solo runner or a relay team.

Run or walk through the beautiful Fox Hill Nature Preserve this fall. Choose from trail runs, a walk, or a kids' race, all supporting local land conservation. Experience deciduous forests, restored prairies, and scenic glacial moraines.

Join the charity trail run or walk in Denmark, Wisconsin. Choose your distance for canicross with your dog or go solo on the wooded trails. The event includes a costume contest and supports the Crisis Cafe.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.

A night running event near Lake Mills, WI on a flat crushed‑limestone rails-to-trails course offering 16 and 31 mile out-and-back distances with required lights, reflective gear, and cupless aid stations.

A winter trail ultrarun in Dousman, Wisconsin on Feb 27-28, 2027 offering 6, 12 and 24 hour solo or relay options, winter trail terrain, warming shelters, hot drinks and a post-race meal.