Trail Running calendar near Williams Bay 2025-2026

The Des Plaines River Trail Races, held in Lake County, Illinois, offer a scenic and fast trail running experience with distances including a Half Marathon, Marathon (Boston Qualifier), 50K, and 50 Mile ultra. Starting and finishing at Half Day Forest Preserve, the course features a flat, wide, crus..

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.

The Fancy Nonsense 25K/50K is a whimsical ultramarathon held in the Palos Trail System near Willow Springs and Lemont, Illinois, about 20 minutes from downtown Chicago. Runners can choose from 25K, 50K, or 5-mile distances on a mostly single-track, 5.5-mile loop course that encourages joy and imagin..

Among the Trees is a scenic running event scheduled for October 25, 2025, in Dousman, Wisconsin. Participants can choose between two challenging distances: 100k and 50k, both set against the beautiful backdrop of the Southern Kettle Moraine Forest along the historic Ice Age Trail. The race begins at..

The Forge Trail Run Festival, scheduled for November 15, 2025, in Lemont, IL, features a variety of trail running events including 10K, 20K (Half Marathon), 30K, and 60K races. Participants will navigate single and double-track trails through scenic woods and gravel paths around the historic Lemont..

The Bucks & Does 13.1 Pointer is a running event taking place in Nashotah, Wisconsin, featuring multiple race distances including a 5K, 10K, and a half marathon (13.1 miles). Participants can enjoy a scenic course primarily on well-groomed trails, with over 60% shaded by trees. The event embraces a..

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 a unique running event taking place in Lake Mills, Wisconsin, on December 5-6, 2025. Participants will tackle an out-and-back course on the scenic Glacial Drumlin State Trail, which features a mostly flat, crushed gravel surface. Runners have eight hours to complete the 50k..

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-track..

The Frozen Assets 5K Run/Walk is a unique event hosted by Clean Lakes Alliance, taking place on a frozen lake in Madison, Wisconsin. Participants can choose to run or walk across the ice of Lake Mendota, enjoying stunning views of downtown Madison and the University of Wisconsin-Madison campus. The..

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 quiet, cold forest environment with frozen ground, the race tests participants' endurance and mental toughness in potentially unco..

The Skunk Ape 806/314 Trail Race is a unique endurance event held at Lowell Park in Dixon, Illinois. Scheduled for March 21, 2026, it features two main race distances: 33.75 miles to be completed in 8 hours and 6 minutes, and 13.5 miles in 3 hours and 14 minutes, along with a relay option. The cours..

The Earth Day 50k is a trail running event held at Veterans Acres in Crystal Lake, Illinois. 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 an eco-friendly approa..

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 race held at Donald County Park in Mt. Horeb, Wisconsin. It features well-marked courses through a scenic rural setting with diverse ecological views, welcoming both newcomers and experienced runners.The event offers distances including 5 km and 15 km, wi..

The Sugar Badger 50/50 and Half is a scenic trail 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, which include trestle bridges,..