Trail Running calendar near Middleton 2025-2026

The Mines of Spain Trail Races, held in Dubuque, Iowa, offer runners three challenging distances: a half marathon, 7-mile, and 4-mile race. Set in the scenic Mines of Spain State Recreation Area, the courses feature diverse terrain including dirt single and double tracks, prairie grass trails, rocky..

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 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 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..

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 Tiger 10 Miler will take place in Byron on Saturday 20 September 2025. You can run 10 miles.

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..

Queen of the Ridge is a women-only endurance running event held on a family dairy farm in Arena, Wisconsin, located in the scenic Driftless Area near Madison. This unique race features a "Last Woman Standing" format where female runners complete a challenging 1 to 1.25-mile loop with at least 250 fe..

The S'more Fun Trail Run takes place at Mirror Lake State Park in Baraboo, Wisconsin, offering a variety of distances including a Mini-Marshmallow Mile for kids 11 and under, 5K trail walk and run, 10K trail run, and a half marathon trail run. The course features scenic views along Mirror Lake, sand..

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.

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 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..

The Mines of Spain 100 is a challenging Midwest trail ultramarathon held in Dubuque, Iowa, set in the scenic bluffs, prairies, and forests of the Driftless Region along the Mississippi River valley. The event offers two distances: 100 miles (five loops) and 100 kilometers (three loops) on a roughly..

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 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..