Trail Running calendar near Waukesha 2025-2026

The "Thanks Sandy" event is a 9-mile trail run held at Kohler-Andrae State Park in Sheboygan, Wisconsin. The course features a mostly flat terrain with a total elevation gain of 509 feet and descent of 485 feet, combining concrete paths, wide trails through campgrounds, shoreline running on Lake Mic..

The New Glarus Woods Trail Run is an annual event held at New Glarus Woods State Park in Wisconsin, part of the Savanna Trail Run Series. The 6th edition features multiple race distances: a 1-mile kids fun run, 5 km, 8 km, and 16 km trail runs. The event supports fundraising for mountain bike trail..

The Run The Rails will take place in Elburn on Saturday 16 August 2025. You can run between 4 and 7 miles.

The Sun Prairie Community 5k is an annual running event held at Sheehan Park in Sun Prairie, Wisconsin. It features a 5K cross-country race that follows the Sun Prairie High School Cross Country Course, providing participants with an authentic cross-country running experience. In addition to the mai..

Run The Hawk Trail Run is a challenging endurance event held at the historic Blackhawk Ski Club in Middleton, Wisconsin. Participants can choose from 3, 6, or 12-hour solo or relay races, aiming to complete as many laps as possible on a scenic 2.25-mile loop featuring 345 feet of elevation gain per..

The Summer Trail Classic will take place in Hoffman Estates on Sunday 24 August 2025. You can run between 4 and 13 miles.

The Naperville Trails Half Marathon & 10K is an annual running event held in Wheaton, Illinois, set for September 6, 2025. Participants can choose between a USATF-certified half marathon or 10K distance, both featuring a flat and fast course that winds through the scenic Danada Forest Preserve on cr..

The Hobo Trail Runs, hosted by Rockford Road Runners, take place at Rock Cut State Park in Rockford, Illinois. This annual event offers multiple trail running distances including 10k, 25k, and 50k races, with options to participate in single races or the challenging Triple Crown series (85k total) o..

Dirt Circus - Chicago is a free community running event held in Crystal Lake, Illinois, celebrating local trail running culture. Organized by UltraSignup, the event features a festive atmosphere with a social run, food, raffle prizes, and an expo showcasing local races, run clubs, brands, and busine..

Last Dot Standing is a unique endurance running event held at Belleville Community Park in Belleville, Wisconsin. Participants alternate running 4.2-mile legs between Belleville and Dot's Tavern, a historic local tavern, with one hour to complete each segment. The race continues hourly until only on..

The Fallinline 125 is a challenging ultramarathon held in Greenbush, Wisconsin, covering approximately 132 miles through the scenic Kettle Moraine State Forest along the Ice Age National Scenic Trail. The course traverses the Northern, Middle, and Southern Kettle units, featuring a mix of rugged sin..

Half Day at the Lake is a unique ultra-running event held in Evanston, Illinois, featuring 6- and 12-hour race options. The race takes place on a scenic 2-mile loop along Chicago’s north shore lakefront path, passing through Evanston’s lakefront and Northwestern University’s campus. The course is a..

The DIRWIN DASH, A Bearded Bash is a 5K run/walk event held annually at Fox River Park in Waukesha, Wisconsin, honoring the memory of Dave Irwin, a beloved guidance counselor and cross country enthusiast. The race features a scenic trail course through the woods, offering a refreshing alternative to..

The Trail Run at Indian Lake is a scenic trail running event held at Indian Lake County Park in Cross Plains, Wisconsin. The race offers two distances: a long course of approximately 10.5 km and a short course of about 5.8 km. The course begins in a restored sedge meadow near the kettle lake formed..

The Lapham Peak Colorama Run/Walk is an annual fall running event held at Lapham Peak State Forest in Delafield, Wisconsin. Celebrating its 36th year in 2025, the event features 5K and 10K races on wide, well-groomed ski and hiking trails. The 5K course tours the park's middle level, while the 10K f..

The Fall Trail Classic - Marengo, IL will take place in Marengo on Saturday 4 October 2025. You can run between 4 and 7 miles.

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..

The Wiglorious Day will take place in Delafield on Sunday 12 October 2025. You can run between 5 and 5 miles.

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..