Trail Running Calendar Wisconsin 2026-2027

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 unique two mile obstacle course at Alsteen Farms featuring real farm chores like tire throwing and calf feeding. Enjoy a yogurt bar and an optional dairy farm tour after the event.

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.

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.

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.

An overnight 10 hour timed trail run at the Millville Bridle Unit in Prairie du Chien, Wisconsin on June 20, 2026. Runners complete repeated 5.25 mile loops on Driftless Area trails, with a single aid station and a 75 person limit.

A multi-duration trail event at Camp Sinawa near Valders, WI featuring a 4.5-mile loop with 330 ft gain per lap. Registration opens Jan 2, 2026; online registration closes June 24 and there is no race-day registration.

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 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 trail event in Solon Springs, WI offering 5K, half marathon, marathon, and a 50/50 Mystery Ultra on the North Country Trail. Each distance is capped at 50 runners and the mystery ultra distance is revealed on course.

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.