Trail Running calendar near Sherwood 2025-2026

The Cliff Runner 10K is an extreme trail running event held in Sherwood, Wisconsin, within High Cliff State Park. Covering a challenging 10-kilometer course, the race features mostly single-track trails with natural obstacles such as rocks, roots, boulders, and hills, accumulating over 500 feet of e..

The Thanks Sandy event is a 9-mile trail run held at Kohler-Andrae State Park in Sheboygan, Wisconsin. The course features a mostly flat terrain with a total elevation gain of 509 feet and descent of 485 feet, combining concrete paths, wide trails, sandy shoreline running along Lake Michigan, marsh,..

The Fallinline 125 is an ultramarathon event held in Greenbush, Wisconsin, covering approximately 132 miles through the scenic Kettle Moraine State Forest along the Ice Age National Scenic Trail. The course traverses the Northern, Middle, and Southern Kettle units, featuring a mix of rugged single-t..

Twisted Roots is a trail running event held at High Cliff State Park in Sherwood, Wisconsin, featuring both half marathon and full marathon distances. Set against the scenic backdrop of Lake Winnebago and the Niagara Escarpment's majestic cliffs, runners experience a mix of technical single tracks a..

The Lapham Peak Colorama Run/Walk is an annual fall running event held at Lapham Peak State Forest in Delafield, Wisconsin. Celebrating its 36th year in 2025, the event features 5K and 10K courses on wide, well-groomed ski and hiking trails, with the 5K covering the park's middle level and the 10K f..

Zachariah's Acres Fall Run, Walk & Roll is a scenic event held in Oconomowoc, Wisconsin, featuring a 5K, half marathon, and a family-friendly 1-mile walk/roll. Set on 125 acres of natural beauty, the course includes tree-lined paths, wildflowers, prairie grass, ponds, and vibrant fall colors. The fa..

The Mosquito Hill Endurance Run is an annual trail running event held at Mosquito Hill Nature Center in New London, Wisconsin. Participants run or walk on a 3.4-mile loop trail featuring wetlands, prairies, forests, and a climb to the top of Mosquito Hill, with about 400 feet of elevation gain per l..

The Bucks & Does 13.1 Pointer is a trail running event held in Nashotah Park, Wisconsin, featuring distances of 5K, 10K, and a half marathon (13.1 miles). The course is primarily wood-chipped with some grassy sections, shaded by trees for a comfortable run, and is run in a counterclockwise direction..

The Fast Eddie 50K and 5K take place at Lapham Peak in Delafield, Wisconsin, celebrating endurance and community while honoring Ed Condon's legacy. The 50K features five loops on the scenic and challenging Blue Loop trail, known for its rolling terrain and beautiful woodland views. The 5K offers an..

The NK50k is an annual 50-kilometer point-to-point trail run held in Greenbush, Wisconsin, along the Northern Kettle Moraine Ice Age Trail. The course features a mix of smooth ski trails, rocky and rooty sections, and reaches the highest point in the Northern Kettle Moraine State Forest, offering va..