Trail Running calendar near Oconomowoc 2025-2026

Soul Crusher is a challenging trail running event held in Crystal Lake, Illinois, offering 5-mile and 10-mile distances. The course, designed by Jeff Lenard, is known as the toughest 5-mile loop in the Midwest, with runners able to complete one or two loops depending on their endurance. The race sta..

The Black Hawk Ridge Trail Run will take place in Mazomanie on Sunday 19 October 2025.

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 Fast Track Cross Country Open is a 3-mile cross country running event held in Schaumburg, Illinois, on the MacNider course near Hoover Elementary School. Open to all ages and abilities, the event features separate women's and men's races. Participants can enjoy running on grass and have the opti..

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, held at Lapham Peak in Delafield, Wisconsin, is an endurance event featuring a 50K ultra and a 5K race. The 50K consists of five loops on the scenic and challenging Blue Loop trail, known for its rolling terrain and beautiful woodland views. The 5K is an out-and-back course on th..

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..

The Arctic Frog Run in Libertyville, IL, is a challenging endurance event held in early December, featuring distances of 50K, 25K, 15K, 10K, and 5K. The scenic course combines pavement, wooded, and crushed limestone trails around the Des Plaines River and Casey Trails, with rolling hills adding to t..

The Frozen Gnome is a challenging winter trail running event held in Crystal Lake, Illinois, at Veteran Acres park. Featuring a "Triple Black Diamond" rated course, the race offers a 50K ultra run, a 10K race, and relay options for teams of two or five. The course consists of a scenic 10K single-tra..

The Frozen Assets 5K Run/Walk is a unique winter event held in Madison, Wisconsin, where participants run or walk entirely on the frozen surface of Lake Mendota. The 5K course offers scenic views of downtown Madison and the University of Wisconsin-Madison campus. Starting and finishing at The Edgewa..

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, the race tests participants' endurance and mental toughness in potentially uncomforta..

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 diverse terrain, including smooth ski trails, rocky and rooty sections, and the highest point in the Northern Kettle Moraine State Forest. R..

The Earth Day 50k is a trail running event held in Crystal Lake, Illinois, at Veterans Acres Park. It offers three race distances: 50 kilometers, 15 miles, and 5 miles, all starting together on a 5-mile loop course featuring single track trails and rolling hills. The race emphasizes sustainability,..

Childish Nonsense is a trail running event held in Palatine, Illinois, at Deer Grove Forest Preserve West. It offers multiple distances including a 50-mile, 50K, 25K, and 10K, with courses consisting of laps on a mostly wide, non-technical trail. Runners encounter a single aid station at the start/f..

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 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..

Rumble on the Ridge is a unique endurance running event held on a family dairy farm in Arena, Wisconsin, within the scenic Driftless Area. Participants run a challenging loop of approximately 1 to 1.25 miles, called "The Drifty Mile," with at least 250 feet of elevation gain. The course changes annu..

The Sugar Badger 50/50 and Half Marathon is a scenic running event held in Belleville, Wisconsin, featuring distances of 50 miles, 50 kilometers, and a half marathon. The race takes place on the flat, soft rail trails of the Badger State Trail and Sugar River State Trail, known for their trestle bri..