Trail Running calendar near Waukesha 2025-2026

The Dawn to Dusk Endurance Run is an ultramarathon event held at Camp Sinawa near Valders, Wisconsin. The race features multiple timed events including 24-hour, 15.5-hour, 8.5-hour (Dusk to Dawn), 8-hour, and 6-hour runs. The course is a 4.5-mile loop primarily through wooded terrain, combining roll..

The Kishwauketoe 5K Cross Country Run takes place in Williams Bay, Wisconsin, starting at the KNC entrance on Highway 67. The course features scenic grass trails through hills, woods, and prairie, offering a natural and challenging terrain for runners. The event includes a 5K run/walk and a children..

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 woodland trails, sandy shoreline running along Lake Michi..

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 the development of mountain bike tr..

Run The Hawk Trail Run takes place at the historic Blackhawk Ski Club in Middleton, Wisconsin. This endurance event features 3, 6, and 12-hour challenges where participants complete as many laps as possible on a scenic 2.25-mile loop with 345 feet of elevation gain per lap. The course includes diver..

The Summer Trail Classic is a trail running event held at Paul Douglas Forest Preserve in Hoffman Estates, Illinois. It offers three race distances: approximately 4 miles, 9.5 miles, and 13 miles, featuring twisting single-track trails that provide a true trail running experience. The event is part..

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 race, both featuring a flat and fast course that winds through the scenic Danada Forest Preserve on crushe..

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 and races. Organized by UltraSignup, this one-day festival features a social group run with options of 3 or 5 miles through scenic Veteran Acres Park. The event fosters camaraderie..

Timely Nonsense is a unique timed running event held in Chicago, IL, at a 58-acre park located at California and Montrose. Participants run a 0.75-mile paved loop for either 6 or 12 hours, with an aid station at the start/finish offering typical ultrarunning fare and additional vendor treats like ho..

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 an ultramarathon event 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 single-t..

Half Day at the Lake is a unique 6- or 12-hour ultra-running event held in Evanston, Illinois, along a scenic 2-mile loop on the lakefront path near Northwestern University. The course features a mix of paved and crushed gravel surfaces, offering beautiful views of the Chicago skyline and the north..

The DIRWIN DASH, A Bearded Bash is a 5K run/walk event held annually in Waukesha, Wisconsin, at Fox River Park. This race honors the memory of Dave Irwin, a beloved guidance counselor and cross country enthusiast from Heritage Christian School. The course features a scenic trail through the woods, o..

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 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 courses on wide, well-groomed ski and hiking trails, with the 5K covering the park's middle level and the 10K f..

The Fall Trail Classic 2.0 is a trail running event held at Marengo Ridge Conservation Area in Marengo, Illinois. It features two races on the same day: a 4-mile run through oak and hickory woodlands, small stream bridges, and restored prairie trails, and a 7-mile run that includes the 4-mile loop p..

Zachariah's Acres Fall Run, Walk & Roll is a scenic event held in Oconomowoc, Wisconsin, featuring a 5K, half marathon, and a family-friendly 1-mile walk/roll. Set on 125 acres of natural beauty, the course includes tree-lined paths, wildflowers, prairie grass, ponds, and vibrant fall colors. The fa..

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..