Trail Running calendar near New Prospect 2025-2026

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..

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 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 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 First Annual Paws for a Cause Canicross & Trail Run/Walk for Charity takes place in Denmark, Wisconsin, offering participants the chance to run or walk scenic wooded trails with or without their dogs. The event features three distance options—2.8, 5.6, and 8.4 miles—catering to all fitness level..

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,..

The Iola Fall Classic Trail Race is a new annual event hosted by the Iola Winter Sports Club in Iola, Wisconsin. It features three trail races—the 25k, 10k, and 5k—set on a mix of single-track and cross-country ski trails. The event emphasizes a family-friendly, fall-running atmosphere with post-rac..

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..

Run for the Hill of It/Run for the Hill-O-Ween is a 5K trail race in Green Bay, Wisconsin, at 500 Beverly Road along the Baird Creek Greenway. Runners cover about 3.1 miles, including Triangle Hill (“The Big Hill”). Halloween theme adds fun, with costumes optional.Also features the Little Hill Racer..

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..

Elver Park Trail Run is held at Elver Park in Madison, WI. The event features 10K, 5K Run/Walk, and a free 1K Kids Fun Run led by a friendly animal. All races begin and end behind the Main Shelter; the 5K uses the western half while the 10K continues to the east for its second half, with clear cours..

Bristol Woods Trail Run takes place in Bristol, Wisconsin at Bristol Woods County Park, hosted at the Pringle Nature Center (9800 160th Ave). The event offers a 5K Trail Run and a 2 Mile Walk, plus junior versions for participants 18 and under. The course runs along the park’s trails, described as a..

Warrior 5K & 8K...Through The Park is a fall trail running event held at Greenfield Park in West Allis, Wisconsin. The weekend offers a 5K Run, 8K Trail Run, a 2.25 Mile Walk, and team options for the 5K and 8K, with cross-country-style scoring across four divisions: White, Green, Black, and Silver...

Run Til You Snowdrop-24 Hour Treadmill Run is a charity endurance event held in Appleton, Wisconsin, at Crunch Fitness (2500 S. Kensington Drive). The fundraiser runs for 24 hours on 24 treadmills to support the Snowdrop Foundation of Wisconsin and families fighting pediatric cancer, honoring the 24..

PROMixed XC Relay is held at Mitchell Park in Brookfield, Wisconsin (19900 River Road). The mixed-gender relay features four runners per team in the order male, female, male, female, with each athlete running 3000 meters. The event, backed by Performance Running Outfitters and USATF Wisconsin, serve..