Trail Running calendar near Madison 2025-2026

ARKTOS : February 28 to March 1, 2026 ARKTOS is a winter trail ultra held in Dousman, Wisconsin (Southern Kettle Moraine Forest). The event offers timed-loop formats in three durations. The race is open to solo runners and relay teams of up..

Trailbreaker : March 29, 2026, Waukesha, WI The Trailbreaker is scheduled for March 29, 2026, in Waukesha, WI, with the main venue at the Schuetze Recreation Center / Frame Park Baseball Stadium. The event has been hosted by the Park Founda..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an endurance running event held in the scenic Kettle Moraine State Forest near Dousman, Wisconsin. Participants can choose from multiple race options including 6-hour, 12-hour, and 24-hour solo..

The Donald Dash Trail Run is a popular trail running event held at Donald County Park in Mount Horeb, Wisconsin. It offers two race distances: a 5K for beginners and a more challenging 15K for experienced runners. The course features divers..

Run the Galena Sky Trail Race on May 16, 2026 at Chestnut Mountain, choosing four hour or eight hour timed formats on scenic looped trails with Mississippi River views. Rack up loops, earn a striking 3D Warrior finisher medal and enjoy a he..

Rumble on the Ridge is a Last Person Standing loop race at a private Arena farm featuring a rugged 1 to 1.25 mile loop with big climbs. Run a lap every 20 minutes until one runner remains, with crew space, hot food and Saturday camping.

Run 50 mile, 50K, or half marathon on scenic flat rail trails in Belleville on May 23, 2026. Enjoy trestle bridges, a quarter mile tunnel, generous cutoffs and post race pizza, beer and swag for finishers.

Explore the rugged trails of Kettle Moraine in LaGrange WI, with ultra options from the 38 Miler up to the 100 Miler, plus relays and a 50K. The mostly trail route includes 65 miles on the Ice Age Trail and the 100 Miler is a Western States..

Run the Whitewater Trail Challenge on June 20, 2026 in Whitewater WI with 10K, half marathon and 50K options along the scenic Ice Age Trail at Rice Lake. Rolling hills and technical footing create a rewarding summer trail test.

Push your limits in Belleville WI Sept 18 to 20 with a weekend of timed endurance races on an out and back route to Dot's Tavern. Choose Last Dot Standing, 24 or 48 hour challenges and chase buckle distances up to 200 miles.