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 starts and finishes at Re..

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 Forge Trail Run Festival, held in Lemont, Illinois, offers a challenging late-fall trail running experience with distances of 10K, 20K (half marathon), 30K, and 60K. The courses start and finish at The Forge and wind through single and double-track trails in the woods, gravel paths, and around t..

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..

The Arctic Frog Run in Libertyville, IL, is a challenging winter endurance event featuring multiple race distances: 50K, 25K, 15K, 10K, and 5K. The course offers a scenic mix of pavement, wooded, and crushed limestone trails around the Des Plaines River and Casey Trails, with rolling hills adding to..

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 and brisk winds, the race offers a unique, rugged atmosphere that tests participants'..

The Muddy Shamrock @ The Forge is an annual trail running event held in Lemont, Illinois, featuring a Trail Half Marathon (approximately 13.1 miles) and a Trail Quarter Marathon (about 6.6 miles). The race courses wind through wooded single and double-track mountain bike trails and gravel paths arou..

The Skunk Ape 806/314 Trail Race, held at Lowell Park in Dixon, Illinois, is a unique endurance event featuring two main 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 an 806 Relay option. The course consists of a 2.25-mile singl..

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..