Trail Running calendar near Nashotah 2025-2026

Badgerland Striders 24-12-6 Hour Runs takes place at Lapham Peak State Park in Delafield, Wisconsin. Runners choose 24-, 12-, or 6-hour formats, with day or night divisions for the shorter races, plus a Distance division for longer goals (marathon, 50K, 50 miles). The course is a 1-mile loop on a ge..

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 one-day, free community trail-running festival in the Chicago area, organized by UltraSignup. The event blends a casual social run with a pop-up expo featuring local race directors, brands, shops, and coaches. Participants choose between two routes, approximately 4.5 miles o..

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..

Fallinline 125 is a two-day ultramarathon in Greenbush, Wisconsin, run through the Kettle Moraine State Forest along the Ice Age National Scenic Trail. Limited to 75 entrants, the main 132-mile event features aid stations and a 48-hour, 46-minute time limit, offering a grueling, scenic challenge acr..

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..

Twisted Roots is a trail running event at High Cliff State Park, near Sherwood, Wisconsin. The weekend features a half marathon and a full marathon traversing rugged single-track, rolling prairie, and scenic spans over Lake Winnebago, with views of the Niagara Escarpment and the Lime Kiln Ruins. Hos..

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 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..

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 Milwaukee Beer Run 5k & .05k takes place in Glendale, Wisconsin, at the Bavarian Bierhaus. The event features a 5k Beer Run/Walk (3.1 miles) and a 54-yard .05k Beer Run/Walk, with a virtual option for remote participants. The course is an out-and-back run along the tree-lined Oak Leaf Trail, fin..

Farmer Ken's Pumpkin Dash 5K takes place in Franksville, Wisconsin (53126). It is a 5K trail run along a grass/dirt path set beside corn and other farm fields, offering a scenic rural landscape. The course runs through agricultural surroundings, giving runners a scenic, rustic experience.Participant..

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..

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,..

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..