Trail Running calendar near Waukesha 2025-2026

Last Dot Standing is a unique endurance running event taking place in Belleville, WI, from September 19 to 22, 2025. Participants will engage in a "last person standing" format, where they must run 4.2 miles to Dot's Tavern and back, with each leg of the race starting every hour on the hour. In addi..

Fallinline 125 is an exciting running event taking place in the scenic Kettle Moraine State Forest, Wisconsin. Participants will embark on a challenging 132-mile course that showcases the beauty of the Ice Age National Scenic Trail. The event aims to promote community engagement and environmental st..

The Half Day at the Lake is an exciting running event taking place in Evanston, IL, featuring both 12-hour and 6-hour races. Set along a scenic 2-mile loop by the lakefront and Northwestern University, this race caters to all experience levels, from seasoned ultra-runners to first-timers. Participan..

The Trail Run at Indian Lake is an exciting running event held at Indian Lake County Park, featuring two course options: a long course of approximately 10.5 km and a short course of about 5.8 km. The event promotes sustainability by adopting a cup-free policy, encouraging participants to bring their..

The Des Plaines River Trail Races feature a variety of endurance events, including a Half Marathon, Marathon, 50K, and 50 Mile race, all set along the scenic Des Plaines River Trail in Lake County, Illinois. Participants will enjoy a flat, wide, crushed gravel trail that meanders through lush forest..

Zachariah's Acres Fall Run, Walk & Roll is a charitable event taking place in Oconomowoc, WI, designed to support children with special needs. The event features a 5K, a half marathon, and a family-friendly walk and roll, all set against the backdrop of 125 acres of beautiful natural scenery. Partic..

Soul Crusher is an exhilarating trail running event taking place in Crystal Lake, IL, featuring challenging 5-mile and 10-mile courses designed by Jeff Lenard. Known for its tough terrain, the race promises a unique experience that will test participants' limits. Runners can expect surprises along t..

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 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 and 5K event will take place on November 15, 2025, at Lapham Peak in Delafield, WI. This race celebrates endurance and community while honoring Ed Condon and supporting the Little Warrior Foundation, which aids children battling cancer. Participants can choose between a challengin..

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 an exciting endurance running event featuring multiple race distances: 50K, 25K, 15K, 10K, and 5K. Set against a scenic backdrop, the course includes a mix of pavement, wooded trails, and crushed limestone paths along the Des Plaines River. This unique win..

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 an exciting ultra-running event taking place in Dousman, Wisconsin, featuring 6, 12, and 20-hour races for solo runners and relay teams of up to four participants. Set against a serene woodland backdrop, the event encourages runners to embrace the challenge of cold weather and the thrill o..