Trail Running calendar near Winona 2026-2027

An overnight 10 hour timed trail race at the Millville Bridle Unit near Prairie du Chien, Wisconsin, run on a 5.25 mile loop. Limited to 75 runners, the event features a single aid station with basic race food and one steep climb with plann..

A mud obstacle trail run at Whitetail Ridge Ski Area with a 1.5 mile course and 10 plus obstacles. Pre registered entrants may receive swag, and the event includes food sales, family activities, outdoor cold showers, and free parking.

Afton Trail Run stages **25 KM** and **50 KM** trail races at Afton State Park on the St. Croix River on July 4, 2026. The event features course maps, staffed aid stations, volunteer support and published results and photos.

Experience trail running through an active working farm in Winona Minnesota. Choose from five distances ranging from 5k to 43k with no cutoffs for the longest event.

Teams of two race head to head over a just under 300 yards obstacle course with dry obstacles and a likely muddy section in West Concord on July 25, 2026. Open to adults 18 and up; registration fee is $15.

A rolling five mile trail race in Spring Lake Park Reserve, Hastings on July 29, 2026, with two figure-eight loops, a midrace water stop, chip timing and post-race refreshments; field limited to 425 and entry is nonrefundable.

An 11 mile trail race on the Douglas State Trail in Oronoco on August 1, 2026. The course runs on paved rail trail under a tree canopy, celebrates a 50th anniversary, and includes a race gift plus post race refreshments.

A trail event in La Crosse, Wisconsin featuring a timed 4.15 mile loop where each runner has up to one hour to finish. Entry options include individual, 2 to 3 person teams, 4 to 6 person teams, and a single-lap entry.

A mountain running event at Mt. La Crosse on August 7, 2026, featuring a 1200 m sprint, a 2 miles trail with 1000 feet vertical gain, a kids race for under 18s, and a ruck challenge with provided weights.

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.

A community fundraiser at Goose Island Campground in Stoddard, WI offering timed 6 and 24 hour running and walking. Participants set their own goals, from a single loop to more than 100 miles in 24 hours.

Experience the unique terrain of the driftless region at Yellow River State Forest. Choose from 5K 10K or half marathon distances and enjoy post race food games and sponsor giveaways.

Trail races at Frontenac State Park offering 5 and 10 mile courses across prairies, single track woods, and scenic overlooks. The cupless event provides aid stations and restroom facilities; participants should carry a water container.

A 5K trail run and walk on September 26, 2026 at Schwertel Family Farms and The Berry Market in Trempealeau WI. The course runs through a corn maze, into a valley and beside a berry patch while a portion of proceeds supports G-E-T Athletes.

A weekend multi-sport event in Yellow River State Forest combining trail running, catch-and-release fly fishing, and craft beer. Organized by Running Rivers, proceeds support habitat improvement and promote responsible outdoor recreation.

A fixed-time trail event in Winona, MN on October 10, 2026 where participants complete 2.50 mile loops between sunrise and sunset. Options include solo runners, up to five-person relays, a family division, meals, camping, and aid stations.

Tour de Essex on October 10, 2026 at Essex Park in Rochester MN features a trail 7k, a road 10k, and an Essex Challenge for runners who enter both. All event profits support trail maintenance.

Trail races on October 17, 2026 in Black River State Forest near Millston Wisconsin, offering 10k, 25k, 50k and an 85k that links all courses. The event includes a winter hat, handcrafted finisher medals and on site camping.

Hixon 50 is a two-day trail running weekend in Hixon Forest near La Crosse, Wisconsin. It offers races from a kids event and 5K and 10K up to 25K and 50K on singletrack with Mississippi River Valley views.

A time based trail challenge at Whitetail Ridge where runners choose a four hour or eight hour effort on repeated five mile single track laps, with a one mile bonus loop opening in the final hour.