Trail Running calendar near Lake Geneva 2025-2026

The Autumn Leaf Run is a 5K trail race held at Oakdale Nature Preserve in Freeport, Illinois. Open to all ages and skill levels, the event offers a scenic course featuring diverse terrain such as wide tree-lined trails, moderate hills, prairie areas, bridge crossings, and single-track trail sections..

Zachariah's Acres Fall Run, Walk & Roll is held in Oconomowoc, Wisconsin, on a scenic 125-acre private property featuring tree-lined paths, wildflowers, prairie grass, ponds, and vibrant fall colors. The event offers a 5K, a half marathon, and a family-friendly 1-mile walk/roll loop with gentle hill..

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..

Wiglorious Day is a Southern Kettle Duathlon held at Lapham Peak State Park in Delafield, Wisconsin. The event features a challenging course consisting of a 5-mile run, a 5-mile bike ride, and a final 5-mile run. Participants can compete solo or as part of a 2-person or 3-person relay team.The run t..

The Race for Open Space in West Bend, Wisconsin, is a trail running and walking event held at the Cedar Lakes Conservation Foundation’s Fox Hill Nature Preserve. Scheduled for October 12, 2025, it offers a 5K trail run, 10K trail run (two loops), a 1-mile trail walk, and a 5K for participants 18 and..

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 it once or twice depending on their endurance. The race sta..

The Palos Park Spooky Shuffle is a 5K and 10K trail run/walk held at Swallow Cliff South Forest Preserve in Palos Park, Illinois. The event features scenic courses through the Sag Valley Trail System, known for its unique topography with ravines and hills uncommon in the Chicagoland area. The 5K cou..

The Over The Vines Wine Run/Walk is held at Over the Vines Vineyard & Wine Barn in Edgerton, Wisconsin. This event offers a 5K timed run, a 5K untimed walk, and a 2K untimed walk, all on a scenic trail featuring grass, gravel, and compacted dirt terrain. Participants must be 21 or older and enjoy fo..

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 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 3.05-mile race held in Schaumburg, Illinois, on the MacNider cross country course near Hoover Elementary School. Scheduled for November 9, 2025, it features separate women's and men's races open to all ages and abilities. The course consists of a short start fo..

The Big Timber XC Challenge is a trail running event held at Camp Big Timber in Elgin, Illinois. Participants can choose between a 3-mile run/walk (one loop) or a 5-mile run (two loops) through a natural wooded area featuring grass, gravel, dirt, and a notable creek crossing with a rope for support...

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 Abominable Trail Race is an exciting autumn trail running event held annually at LG Ziplines and Adventures in Lake Geneva, Wisconsin. It features three race distances: 5K, 15K, and 30K, with the 30K available for individual runners or teams of 2 to 4 in relay format. Participants navigate chall..

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 Whitewalker Ultra 100k is a challenging winter ultramarathon held in Palmyra, Wisconsin, starting at the Emma Carlin Trailhead. Participants complete two 50k loops within 24 hours, traversing the Ice Age Trail to Whitewater and returning, then heading to the Scuppernong Trails and back. The race..