Trail Running Calendar Wisconsin 2026-2027

The Fight for Air Stair Climb returns to Milwaukee's 411 East Wisconsin Center on March 21, 2026. Participants can choose to climb the 30-story building once, twice, or take on the Power Hour challenge. A virtual option is also available fo..

Enjoy a scenic seasonal run through the trails of the Brown County Reforestation Camp followed by a fresh pancake breakfast. Participants can choose between a 5K or a family fun run with sweet treats waiting at the finish.

The Trailbreaker will take place in Waukesha on Sunday 29 March 2026. You can run between 3 and 26 miles.

Event Details The NK50k is an annual fun run scheduled for April 11. It features 50K and 25K distances. The event is a point-to-point tour on the Ice Age Trail in the Northern Kettle Moraine State Forest, starting from the Ridge Road Trailh..

A spring trail event at the Iola Winter Sports Club offering **5k** and **15k** courses on ski trails and singletrack, plus a free kids 1k when weather permits. Food and drinks will be available in the Chalet and entry fees change after Mar..

Explore the early spring trails at the Bird Sanctuary, a managed brush prairie on the North Country Trail. Choose between a scenic 10k or a 20k that tours the entire wildlife area, both on 99.9% single-track. The courses offer a mix of open..

Experience a unique chip timed race in Belgium featuring road and trail sections through Harrington Beach State Park. Choose between a fast 5k road course, a 10k hybrid trail run, or a scenic half marathon with Lake Michigan views.

The Chippewa Trail Races offer a classic trail running experience on Wisconsin's scenic Ice Age Trail. Choose from four distances, including a 50K relay, on forested single-track paths. All finishers get a commemorative print to celebrate t..

Experience the diverse landscapes of Shiocton at the Navarino Nature Center Trail Run. Run or walk through forests and across bog boardwalks to support environmental education and local trail improvements.

A trail race at Donald County Park in Mount Horeb on May 2, 2026, offering 5 km, 15 km and a Kids One Mile Fun Run; chip timing, aid stations, awards, and proceeds benefit Friends of Donald Park for trail maintenance.

Choose your challenge: a 10-mile or 20-mile trail race through Willow River State Park. The course winds along grass and gravel paths, with aid stations and a cupless policy. It's a scenic run with different start times for each distance.

Event Details The Popple Shoot Trail Races take place on Saturday, May 9, 2026. The event is organized by Big Slo Running and net proceeds are donated to local charities. The races start and finish at the Wild River Campground, located at 8..

A low-impact trail event at Lapham Peak Park offering distances from a Kiddos 1K to a half marathon, with ruck and walk options, cupless aid stations, and proceeds benefiting Tall Pines Conservancy.

Experience the beauty of spring at Bristol Woods County Park with a hilly trail run or hike. Support environmental education while enjoying peak wildflower season on scenic dirt paths in Wisconsin.

Test your fitness at the Hixon Trail Series in La Crosse. This monthly four part timed trail running series takes place from May through August at Old Quarry Road.

The Sugar Badger 50 Miles is a trail ultramarathon scheduled for May 2026. Organized by Ten Junk Miles Racing, it focuses on a community atmosphere on the trails. The event is a single 50-mile distance challenge.

Trail run and walk in Cable on rolling single track through Bayfield County Forest, with 5K, 10K and half marathon options plus age group awards and local homemade bread and jam for all participants.

Experience a scenic point to point run from Plover to Amherst along the Tomorrow River Trail. This half marathon concludes at the Central Waters Brewing Co for a memorable finish in Wisconsin.

The First Mondays Summer Trail Series is a summer trail running event at the Iola Winter Sports Club. A different 5 km course is featured each month in June, July, and August. The series includes a vertical hill challenge and a kids race.

The Jack Lake Crazy Eights Trail Run will take place in Deerbrook on Saturday 6 June 2026. You can run 10 kilometers.