Trail Running calendar near Brookfield 2025-2026

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 races, as well as 12-hour and 24-hour relays. The course fe..

The Sugar Badger 50/50 and Half Marathon is a scenic trail running event held in Belleville, Wisconsin, featuring distances of 50 miles, 50 kilometers, and a half marathon. The course follows the flat, soft rail trails of the Badger State Trail and Sugar River State Trail, showcasing trestle bridges..

Kettle Moraine is a renowned ultra marathon held in LaGrange, Wisconsin, featuring multiple race distances including a 100-mile, 100K, 50K, 38-mile, and a 100-mile relay. Established in 1996, it is one of the oldest 100-mile races in the U.S. The course is 100% trail, with about 65 miles on the scen..

2026 Whitewater Trail Challenge, part of Spartan Trail, takes place on the Rice Lake Nature Trail in Whitewater, Wisconsin. The event offers three distances: 50K, 21K (half marathon), and 10K. The course is an out-and-back segment of the Ice Age Trail, a 1,200-mile National Scenic Trail that showcas..

Cliff Runner 10K is a challenging 10-kilometer trail race held in Sherwood, Wisconsin at High Cliff State Park. The course takes runners along mostly single-track trails through the park’s rugged terrain, featuring rocks, roots, boulders and rolling hills with more than 500 feet of total elevation g..