Trail Running calendar near Sheboygan 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 Fruitland Trail Run/Walk takes place in Whitehall, Michigan, offering 5K and 10K trail run/walk events on a challenging, 100% asphalt-free course. The route winds through pine forests, creek ridges, rolling hills, and sandy terrain, providing a scenic and natural running experience. Participants..

The Jazz Blueberry Trail Run/Walk is an annual event held at Jazz Blueberry Farm in Shelby, Michigan. Scheduled for July 27, 2025, it features a 5K run/walk, a 10K run, and a 1-mile fun run. The course offers a cross-country style experience with trails, grass, and dirt paths, providing a scenic and..

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 North Country Trail Run is a premier trail running event in the United States, featuring multiple race distances including a 50 Mile Ultra Marathon, 50K Ultra Marathon, 26.2 Mile Marathon, and a 13.1 Mile Half Marathon. Scheduled for August 23rd and 24th, 2025, this event is known for its impres..

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..

The DIRWIN DASH, A Bearded Bash is a 5K run/walk event held annually in Waukesha, Wisconsin, at Fox River Park. This race honors the memory of Dave Irwin, a beloved guidance counselor and cross country enthusiast from Heritage Christian School. The course features a scenic trail through the woods, o..

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..

Among the Trees is an ultramarathon event held in Dousman, Wisconsin, featuring 100k and 50k race distances. Set within the scenic Southern Kettle Moraine Forest along the historic Ice Age Trail, the course offers runners a challenging and picturesque experience amid vibrant fall colors. Both races..

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 Quiet Silence 50k is an ultramarathon held in Lake Mills, Wisconsin, featuring an out-and-back course on the Glacial Drumlin State Trail. Starting at Rotary Park in Lake Mills, runners head west to the trail's terminus in Cottage Grove, covering a mostly flat, crushed gravel path. Participants h..

ARKTOS is a challenging ultra running event held in Dousman, Wisconsin, featuring 6, 12, and 20-hour race options for solo runners or relay teams of up to four. Set in a cold, wooded environment with frozen ground and brisk winds, the race offers a unique, rugged atmosphere that tests participants'..

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..

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..