Trail Running Calendar Wisconsin 2025-2026

The Golden Pines Trail Run at Machickanee, held in Abrams, Wisconsin, offers an evening trail running and hiking experience through the scenic Machickanee Hiking and Ski Trails. Participants can choose from 7K or 11K distances, with options..

Challenge yourself on the Trout Brook 10 mile trail through Willow River State Park, featuring single track, steep climbs, stairs, and a scenic waterfall. Perfect for experienced trail runners seeking tough terrain and great views.

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,..

Event overview The Gandy Dancer Marathon takes place in Luck, Wisconsin on Saturday, October 11, 2025. The event weekend includes multiple races and is a fundraiser for the Luck Fire Department. Events offered: Marathon Half Marathon 5k Ru..

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 o..

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. T..

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-perso..

Event details The Black River Trail Classic takes place on October 18, 2025, in Black River State Forest, Millston, WI. This is the 9th running of the event. Distances offered are: 85K 50K 25k 10k Registration closes Wednesday, October 15..

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 emphasi..

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..

Conquer Triangle Hill at Run for the Hill of It on October 18 in Green Bay, a scenic 5K trail run with kids, dog walk, and virtual options. Proceeds support Baird Creek Greenway and finishers get shirts, snacks, and king and queen honors.

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 woodl..

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..

Run a 50 mile point to point through Door County's peak fall colors from Gills Rock to Sturgeon Bay on October 25, 2025. Fast rolling roads, supportive aid stations, and an epic finish line party make this a bucket list autumn ultra.

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..

Push your limits on scenic single track trails at the Icebox timed challenge, choosing a 4 hour or 8 hour option to rack up as many miles as you can. Start between 6 and 8 am and tackle a final one mile loop in the last hour.

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 un..

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 fe..

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 Wisco..

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 sco..