Trail Running calendar near Baraboo 2026-2027

Experience a seven month trail adventure through the scenic parks of Waukesha County. Choose from running, walking, or rucking across distances ranging from 5K to a Half Marathon.

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..

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.

Event Overview The Friends of Yellow River State Forest Trail Run is the seventh annual running event held in the state forest. It takes place over two days, with events on May 8 and 9, 2026. The event is organized by the Friends of Yellow..

Rumble on the Ridge is a backyard ultra held on a private farm near Madison. Runners tackle a secret 1+ mile loop every 20 minutes until only one remains. The event supports the creation of a new local trail network.

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.

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.

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.

A trail run at Blue Mound State Park on June 6, 2026 offering 10K and 18K courses over varied single-track and ski trails; proceeds benefit the Friends of Blue Mound State Park.

An annual trail ultra held each June with 100 mile, 100k, 50k and 38 mile options; much of the course runs on the Ice Age Trail. Registration for 2026 is by Ultrasignup lottery with a waitlist and early-invite options.

Experience the glacial landscapes of Wisconsin at the Whitewater Trail Challenge. Run along the historic Ice Age Trail with 10K, Half Marathon, and 50K distances starting from the scenic Rice Lake Nature Trail.

A trail running event at Devil's Lake near Baraboo, WI on July 11, 2026, offering distances from 10K to 50 miles, marked courses with aid, post-race food and a finisher medal.

This 10k walk/run explores the trails of Kettle Moraine State Forest in Wisconsin. It's a cup-less event with water refills and snacks provided. A portion of donations supports The Salvation Army.

Experience the unique Run Until Done format on a 4.15 mile trail loop in La Crosse. Participate as an individual or in teams of up to six people to test your endurance against the clock.

Test your endurance at Prairie du Chien's first backyard ultra featuring a 4.167 mile trail loop through La Riviere Park. Run one lap every hour until only one participant remains or enjoy a relaxed one lap fun run.

This annual community event in Sun Prairie features a 5k race and a kids' fun run, with a course on neighborhood bike paths. Proceeds go directly to support the local high school cross country team.

Experience the beauty of New Glarus Woods State Park with trail races ranging from 5k to 16k. This annual event features forested loops and prairie views while supporting park conservation efforts.

Run the Hawk offers timed trail challenges on a scenic 2.25-mile loop at Wisconsin's Blackhawk Ski Club. Choose from 3, 6, or 12-hour solo or relay events, or a shorter 1.7-mile fun run. The event features unique course landmarks, team tent..