Trail Running calendar near Iola 2026-2027

Point-to-point trail runs on the Northern Kettle Moraine Ice Age Trail near Greenbush WI with 25K and 50K options, aid stations, drop bag access for 50K runners, and post-run food at the Group Camp shelter.

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..

Participate in a two mile run or walk through the scenic 120 acre Southern Door School campus. Enjoy a course of gravel and woodland trails while supporting local students and staff in Brussels Wisconsin.

Experience the diverse landscapes of Shiocton at the Navarino Nature Center Trail Run. Run or walk through forests and across bog boardwalks to support environmental education and local trail improvements.

WausaUltra at Sylvan Park in Wausau features a 4.167 mile mostly trail loop offered as a Limitless backyard event, Solo, Double, and a free kids race over May 1 to May 3, 2026.

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.

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.

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.

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.

Experience a grassroots wilderness race at the Underdown Trail system in Merrill. Choose between various trail running and mountain bike distances featuring glacial hills, singletrack paths, and scenic boardwalks.

Experience a relay adventure through the single track trails of Nine Mile Forest in Wisconsin. Choose from various team sizes to run through pine and birch forests with overnight camping and a communal village atmosphere.

Trail marathon and half marathon at High Cliff State Park featuring technical singletrack, prairie sections and Lake Winnebago views. The event is cupless with aid stations and proceeds supporting the park.

Explore the scenic trails and steep hills of Mirror Lake State Park with several distances available. Finish your race with refreshments and s'mores around a campfire while supporting local park projects.

Join the charity trail run or walk in Denmark, Wisconsin. Choose your distance for canicross with your dog or go solo on the wooded trails. The event includes a costume contest and supports the Crisis Cafe.

Run scenic glaciated woodlands and rolling ridges at the Black River Trail Classic in Millston WI with options from 10k to the 85k ultra. Expect well marked trails, hot finish line food, a winter hat and wooden finisher medals.