Trail Running calendar near Iola 2026-2027

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..

An evening trail race at Nine Mile County Forest with 5K, 10K and 20K lap options on singletrack and ski trails. The looped course requires lights and provides on-course water and nutrition at key points.

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 marathon at High Cliff State Park near Sherwood, WI featuring technical singletrack, prairie sections and views of Lake Winnebago, run as a cupless event with local park support.

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.

A fall ultramarathon on the Ice Age Trail near Greenbush, Wisconsin offering 50 mile and 50K out and back courses. Aid stations are spaced four to eight miles and the event is cupless with reusable cups provided at check in.

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.

Trail running event on October 31, 2026 at the Greenbush trail system near Glenbeulah, WI. Choose a 5K one loop or a 10K two loop course; chip timing is provided and a park sticker or daily pass is required.

A point to point trail run on the Northern Kettle Moraine Ice Age Trail in Greenbush, WI on April 3, 2027. Offers 50K and 25K distances with aid stations and transport to the start; presented as a fun run not a race.

At Sylvan Park in Wausau, WI a 4.167 mile mostly-trail loop is used for three options over May 7 to 9, 2027. Runners can repeat the loop in a backyard style event or choose one or two loop distances; a short kids race is included.

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.