Trail Running Calendar Wisconsin 2025-2026

Take in wooded trail views at the Fall Into Fall Trail 5k in Janesville, then stay for live music, food trucks and beer and wine tasting at the festival. Run or walk a fun, scenic course and celebrate the season with community festivities.

Enjoy a fall run, walk and roll through 125 acres of prairie, ponds and fall color at Zachariah's Acres in Oconomowoc. Choose 5K, half marathon or a family one mile loop while supporting nature based programs for children with special needs..

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.

Run scenic glaciated woodlands and rolling ridges at the Black River Trail Classic in Millston WI with options from 10k to the 85k ultra. Expect well marked trails, hot finish line food, a winter hat and wooden finisher medals.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 17 October 2026. You can run between 5 and 10 kilometers.

Experience peak fall colors on Wisconsin's scenic Door County roads at The Fall 50, featuring a challenging 50 mile solo option or a fun relay for teams. Enjoy autumn views and community camaraderie on this one day running celebration.