Trail Running calendar near Iola 2026-2027

The Dormie Challenge is Portage County's first ultra marathon on May 30, 2026 at UWSP campus in Stevens Point. It offers 12 hour and 6 hour endurance events with limited fields, aid stations, timing, and medical support.

A farmer inspired obstacle course of about 2 miles at Alsteen Farms in Lena, WI on May 30, 2026. The course includes farm chores like feeding calves and climbing through a tractor, with a yogurt bar and optional farm tour. $25 entry.

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.

A three night trail series at Iola Winter Sports Club with changing 5K courses, a kids 1k and a vertical challenge on ski jump hills. Races are untimed and each night has a per event fee of $10.

A 10 km trail run on single track mountain bike and snowmobile trails in Deerbrook, WI on June 6, 2026. Online registration is available through June 5 and the entry fee for the 10 km is $40.

Push your limits at the Dawn to Dusk Endurance Run in Valders, Wisconsin, a timed trail event offering 6 to 24 hour formats on a scenic 4.5 mile lakeside loop. Live tracking and on site cabins make it an ideal weekend of endurance and camar..

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.

Cliff Runner 10K on July 19, 2026 in Sherwood, WI is a 10K trail run on mostly single track with rocks, roots, boulders and over 500 feet of elevation gain. Registration includes a T shirt and finisher medal and a share of proceeds supports..

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.

Underdown Trail Races in Merrill, Wisconsin on August 15, 2026 offer backcountry singletrack running and mountain biking across distances from a half marathon to 111 miles. Courses are well marked, supported by aid stations, and proceeds su..

A team trail relay on September 18-19, 2026 at Nine Mile Forest near Wausau, WI, featuring 117 total miles, single track trails and overnight camping. Multiple team formats are offered and Ragnar Village provides food, music and camping ame..

Trail half and full marathons at High Cliff State Park in Sherwood, WI, featuring lake views, technical singletrack and prairie sections. The event is cupless, provides aid stations and a post race pasta buffet.

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.

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.

A new annual trail race at Iola Winter Sports Club on 10/17/2026 offering 25 km, 10 km and 5 km courses on singletrack and ski trails, with aid stations, post-race snacks, medals and age-group awards.

Point to point runs on the Northern Kettle Moraine Ice Age Trail near Greenbush, WI. Options include 50K and 25K with aid stations, drop bag access for the 50K, and bus transport to the start.

WausaUltra at Sylvan Park features a 4.167-mile mostly-trail loop offered as Limitless (repeated loops until one runner remains), Solo (one loop) and Double (two loops), plus a short kids' race.

Paws for a Cause in Denmark WI on October 16, 2027 offers canicross and solo trail run or walk options of 2.8, 5.6, and 8.4 miles, with proceeds benefiting Crisis Cafe.