Trail Running calendar near Whitewater 2025-2026

Run the Fox Valley Winter Challenge 10K at Hickory Knolls in St. Charles on Mar 22, 2026, over mixed trails and rolling climbs to test your pace. Finishers earn winter swag and a medal, plus extra gear for completing the series.

Join Trailbreaker in Waukesha for a scenic trail and road race offering distances from a marathon to a kids 1K, with ruck options and a Run Any Distance challenge. Family friendly and fundraising for local parks.

Run the NK50k in Greenbush, Wisconsin on April 11, 2026. Choose 50K or 25K point to point routes across rolling ski tracks, rocky Ice Age Trail sections and lofty ridgelines, with aid stations, shuttle service and post run food; expect to b..

Join the Earth Day trail run at Veterans Acres in Crystal Lake offering 50K, 15 mile and 5 mile options on a rolling 5 mile single track loop around the pond. Enjoy homemade aid station treats and a friendly, eco minded race atmosphere.

Run 10K, 25K, 50K or 50 Miler loops at Deer Grove Forest Preserve West in Palatine. Mostly wide non technical trails, a single aid station, pacers allowed for 50 Miler after four loops, and on course shenanigans promise a fun day.

Run under the stars at Moonlight Meltdown on April 25 in Belgium WI, with chip timed 5k road and a Sunset Safari 10k including a trail through Harrington Beach State Park. Shirts, post race food and a finish party at KYOTES.

Run rolling prairie, single track and sandy hills at the Donald Dash in Donald County Park near Mount Horeb, WI. Choose 5 km or 15 km and support Friends of Donald Park as proceeds fund trail upkeep.

Join the Sugar Badger 50/50 and Half in Belleville, WI for flat, scenic out and back runs on the Badger State and Sugar River State Trails with 50 mile, 50K and half marathon options. Expect trestle bridges, a quarter mile tunnel, aid stati..

Kettle Moraine returns June 13 and 14 2026 in LaGrange Wisconsin, offering 100 mile, 100K and shorter trail distances with plenty of Ice Age Trail scenery. The 100 mile serves as a Western States qualifier, making this a prime summer ultra.

Run the scenic Ice Age Trail near Rice Lake in Whitewater, Wisconsin on June 20, 2026. Choose a 10K, 21K half marathon or 50K and tackle varied, rewarding single track through classic summer forest scenery.

Experience Dances with Dirt Devil's Lake, a midsummer trail run on scenic glacial terrain near Baraboo, Wisconsin. Choose distances from 10K to 50 miles and enjoy aid stations, a finisher medal and post race food and a cold brew.

Tackle rugged trails at the GristMill Grind in Franklin Creek State Natural Area, featuring 5K and 10K routes with creek crossings, bluffs and forest canopy. All proceeds support Franklin Creek conservation and park improvements.

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..