Trail Running Calendar Wisconsin 2026-2027

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.

Blue Mound Trail Run on June 6, 2026 in Blue Mound State Park features 10K and 18K trail races on single-track and ski trails, and serves as a fundraiser for Friends of Blue Mound State Park.

Experience Door County's first trail run at the Crossroads at Big Creek Nature Preserve with 2K 5K or 10K courses that reward participants with a native tree.

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 Wisconsin Northwoods with trail races ranging from 5 km to 50 km. Run through old growth forests and enjoy panoramic views of Lake Superior at this community fundraising event.

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.

Multi distance endurance event at Camp Sinawa near Valders, WI offering 24 hour, 15.5 hour, 8 hour, 6 hour and dusk to dawn formats on a 4.5 mile loop with 330 ft gain per lap.

Run a half marathon, a 5K run or walk, or a 1K kids Cubbie Run in Minocqua on June 27, 2026. Most of the course follows the Bearskin Trail and proceeds benefit the Lakeland Pantry.

This cross country run on July 4th in Williams Bay offers a 5K on grass trails through the Kishwauketoe Nature Conservancy. A kids' quarter-mile event is also available. Registration is online only, with awards for top age-group finishers.

A community July 4 event in Land O' Lakes with a multi-surface 5K and a youth 1K fun run; proceeds support Great Headwaters Trails and the local playground.

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.

A locally run trail event in Solon Springs, Wisconsin offering a 5K, half marathon, marathon, and a 50/50 mystery ultra on the North Country Trail, each limited to 50 entrants.

Take on the Cliff Runner 10K on July 19, 2026 at High Cliff State Park, a rugged singletrack course with rocks, roots and steep climbs. Registration includes a Cliff Runner tee and finisher medal, with proceeds to Purdy Nature Preserve.

Experience the sunset at Nine Mile Recreation Area with a series of trail runs on single track mountain bike paths. Choose from multiple distances and navigate technical terrain using your own lights as the sun goes down.

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.

Challenge yourself on the stairs of Giant Pine Mountain. Choose from a single climb, multiple repeats, or a new combination with a trail run. This chip-timed event in Iron Mountain offers different formats for testing your endurance.

Thanks Sandy is a *9 mile* trail run at Kohler-Andrae State Park near Sheboygan, WI, featuring beach, marsh and cordwalk sections, a three hour cutoff, one on-course aid station and post-run snacks with dietary options.