Trail Running Calendar Wisconsin 2026-2027

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.

This 17th annual trail run offers 2K, 5K, and 10K distances through the Crossroads at Big Creek Nature Preserve. Participants receive a native tree and post-race snacks, with all proceeds supporting environmental education.

A multi-distance trail event near LaGrange, Wisconsin on June 13–14, 2026, featuring 100% trail courses and a lottery entry system. Distances range from 50K to 100 miles and the 100 mile finish in 30 hours qualifies for Western States.

A fundraising trail event in Bayfield, Wisconsin on June 13, 2026 featuring 50K, 25K, 10K and a 5K fun run with obstacle course. The looped course uses singletrack and ski trails and offers views of Lake Superior and the Apostle Islands.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

A trail running event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 10K, half marathon and 50K on rolling hills and well established trails.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

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.

A cross-country event in Williams Bay featuring a 5K run/walk and a children's quarter mile walk/run. The course follows grass trails through hills, woods and prairie, with parking and restrooms provided.

A midsummer trail and road event at Devil's Lake near Madison on July 11, 2026, offering distances from 10K to 50 miles with marked courses, aid stations, finisher medals, post-race food and a brew, and overall and age group awards.

Multiple out-and-back races on the North Country Trail in Solon Springs, WI including a 50/50 Mystery Ultra. Each distance is limited to 50 runners and the event is described as locally run.

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.

An evening trail race at Nine Mile County Forest using a 5K lap format to offer 5K, 10K, and 20K options on single-track and ski trails; lights are required since the run begins at sunset. Kids events take place the following day.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

Run along Lake Michigan's shoreline in this evening 9-mile trail event at Kohler-Andrae State Park. The course features sand, boardwalks, and forest trails under the sunset. Stay afterwards for snacks and celebration by the beach.

Underdown Trail Races The Underdown Trail Races are grassroots trail runs and mountain bike races. They take place in Merrill, Wisconsin on the Underdown Trail system. The location is 6 miles off Highway 51. The running event offers three d..

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.

Run The Hawk is a looped trail event at Blackhawk Ski Club near Middleton, WI offering 3, 6 and 12 hour lap challenges on a 2.25 mile loop and a shorter 1.7 mile fun run. The course features steep climbs, single track and a spring pool.

A small-field ultramarathon on the Ice Age National Scenic Trail in Chequamegon-Nicolet National Forest near Westboro, WI, offering 100 mile, 100k, and 50k options with camping add-ons and a multi-tier rollover policy.

Trail races in St. Croix Falls on August 29, 2026 offering marathon, half marathon and 10K on mixed single track and paved surfaces. Online registration runs November 28, 2025 to August 25, 2026 with a 150 runner limit and no refunds.