Trail Running calendar near Oconomowoc 2025-2026

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 diverse terrain including prairie, single track, sand, slick bridg..

The Prickly Pine Jackpot 24 Hour will take place in Dousman from Saturday 2 May 2026 to Sunday 3 May 2026. You can run between 6 and 24 kilometers.

Rumble on the Ridge is a challenging Last Person Standing ultrarunning event held on a historic dairy farm near Arena, Wisconsin, in the scenic Driftless Area. Participants run a 1 to 1.25-mile loop called "The Drifty Mile," featuring 250-300 feet of elevation gain over mixed terrain including grave..

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..