Trail Running calendar near Belleville 2025-2026

Last Dot Standing at Belleville, Wisconsin, organized by Ten Junk Miles Racing, kicks off at Belleville Community Park. The LMS format features a 4.2-mile out-and-back course between Belleville and Dot's Tavern, a 70-year-old tavern off the trail; each leg must be completed in one hour, with the nex..

The Tiger 10 Miler is an annual trail race held at Byron Forest Preserve and the Nardi Equine Prairie in Byron, Illinois. The 8th edition of this event features a challenging 10-mile course with twists, turns, and hills through scenic natural areas. Participants receive a custom finisher's medal and..

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..

Hindsight Ultra Trail Runs, held in Dixon, Illinois, offers a grassroots ultra running experience with distances of 25K, 50K, 100K, and 100 miles. The course features a 7.85-mile loop combining roughly 50% singletrack, 30% grassy meadows, and 20% gravel paths, with about 6,200 feet of elevation gain..

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 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..

The Swiss Valley Trail Races, held in Peosta, Iowa, offer runners three distance options: 5.2 miles, 25K, and 50K. Set within the scenic Swiss Valley Nature Preserve, the course features rugged terrain, creek crossings, and steep inclines, with each 5.2-mile loop climbing approximately 875 feet. The..

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 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..

October 4-5, 2025, The Hennepin Hundred is Illinois’ only point-to-point, all-trail ultramarathon, running from Sterling along the Rock River to Colona near the Mississippi and following the 104-mile Hennepin Canal State Trail through northwest Illinois’ historic locks, lift bridges, and scenic farm..

Autumn Leaf Run is a 5K trail race held in Freeport, Illinois, at Oakdale Nature Preserve. The course loops through diverse terrain, including wide tree-lined trails, moderate hills, prairie areas, bridge crossings, and several single-track sections. The start and finish are in close proximity, and..

The Trail Run At Indian Lake takes place on Saturday, October 4, 2025, at Indian Lake County Park in Cross Plains, WI (8183 State Highway 19). Registration for the 2025 race is open. Listed entry fees are shown as $30 or $20, with a youth price of $10 for ages 0-20. A free kids run is offered and d..

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..

Wiglorious Day is a Southern Kettle Duathlon held at Lapham Peak State Park in Delafield, Wisconsin. The event includes three distances: a 5-mile run, a 5-mile bike, and a final 5-mile run, with options for solo competition or 2- or 3-person relays (Soulo, or teams). The run takes place on wide, gro..

Race For Open Space is a West Bend, Wisconsin trail running event at Cedar Lakes Conservation Foundation's Fox Hill Nature Preserve. It offers a 5K trail run, a 10K trail run (two loops), a 1-mile trail walk, and a 5K for ages 18 & under. The course traverses deciduous forest, restored prairieland,..

Mines of Spain 100, held in Dubuque, Iowa, offers 100-mile and 100-kilometer ultramarathons on October 17-18, 2025. Set in the driftless region’s bluffs, prairies and forests above the Mississippi River valley, it delivers a true Midwest trail experience. The course is described as a ~20‑mile loop f..

Soul Crusher is a trail-running event in Crystal Lake, Illinois, offering 5- and 10-mile options. Runners navigate single-track forest trails through Veteran Acres and Sternes Woods, with a course described as challenging, fun, and bone-decorated. The start line sits in the middle of the park at a s..

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..

Black Hawk Ridge Trail Run is a trail-running event held in Mazomanie, Wisconsin, at the Black Hawk Unit of the Lower Wisconsin State Riverway. The race offers two distances, 8K and 16K, inviting runners of varied experience to tackle woodland and river-adjacent trails. Described as a scenic and his..

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..