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Trail Running calendar near Sheboygan 2026-2027

We have found 22 Trailruns within 80 miles of Sheboygan. See below where and when you can find the races.

First Annual Paws for a Cause Canicross & Trail Run/Walk for Charity

Denmark - 41 mi from Sheboygan

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.

Wisconsin Trail Series

Oconomowoc - 59 mi from Sheboygan

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.