Trail Running Calendar Wisconsin 2025-2026

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..

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 Black River Trail Classic, held in Millston, Wisconsin within the Black River State Forest, is a trail running event featuring distances of 85K, 50K, 25K, and 10K. Celebrating its 9th year in 2025, the race offers a scenic course with ridge views and vibrant fall colors. Participants receive a w..

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..

Door County Fall 50 is a point-to-point road ultramarathon in Wisconsin’s Door County, running from Gills Rock to Sturgeon Bay. The 50‑mile course unfolds through fall colors and scenic villages, with rolling hills and views along the route. The event includes a solo division (and a relay option) an..

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..

The Icebox 480/240 is a timed endurance running event held at Whitetail Ridge in River Falls, Wisconsin, near the Twin Cities. Participants choose between a 4-hour (240 minutes) or 8-hour (480 minutes) challenge, running multiple loops of a scenic single-track trail approximately 5 miles per loop. I..

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..

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..

The Buck Rut Run is a 5K trail race held at Minocqua Winter Park in Minocqua, Wisconsin. This marks the event’s 30th edition. The course runs through the park’s trail system, offering a forested, scenic route (course map available).Early fees are $25 adults/$20 ages 1-18, increasing to $30/$25 mid-s..

Pen Park Trails Fest is a trail running event held on November 8, 2025, at Peninsula State Park in Fish Creek, WI. The event offers two race distances: 30K 14K Online registration is open May 15 through November 5, with in-person packet pickup on November 7 (4-7 pm) and November 8 (7-8 am) at Wel..

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...

NCTRaces: 15x is a Last Runner Standing ultra held at Palmer's Landing in Solon Springs, Wisconsin, along the North Country Trail. The course is a 1-mile out-and-back loop (½ mile out, ½ mile back) attempted in 15-minute intervals; any runner who cannot finish within the window is eliminated. The St..

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..

Fast Eddie 50k/5k takes place at Lapham Peak in Delafield, Wisconsin. The event offers a challenging 50K consisting of five loops on the Blue Loop, featuring rolling terrain and woodland scenery, alongside a 5K out-and-back on the same trails. Now in its inaugural 50K and fourth year for the 5K, the..

The Bucks & Does 13.1 Pointer is a trail running event held in Nashotah Park, Wisconsin, featuring distances of 5K, 10K, and a half marathon (13.1 miles). The course is primarily wood-chipped with some grassy sections, shaded by trees for a comfortable run, and is run in a counterclockwise direction..

The Abominable Trail Race is an exciting autumn trail running event held annually at LG Ziplines and Adventures in Lake Geneva, Wisconsin. It features three race distances: 5K, 15K, and 30K, with the 30K available for individual runners or teams of 2 to 4 in relay format. Participants navigate chall..

The Quiet Silence 50k is an ultramarathon held in Lake Mills, Wisconsin, featuring an out-and-back course on the Glacial Drumlin State Trail. Starting at Rotary Park in Lake Mills, runners head west to the trail's terminus in Cottage Grove, covering a mostly flat, crushed gravel path. Participants h..