Trail Running calendar near Sherwood 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.

The 17th Annual Crossroads Trail Run offers 2K, 5K and 10K trail courses at Crossroads at Big Creek Nature Preserve in Sturgeon Bay with chip timing, awards and proceeds supporting environmental education.

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 run and walk at Lapham Peak State Forest on July 11, 2026, raising funds for prairie management; events for adults and youth, first 100 registrants receive a T-shirt and run winners receive awards.

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..

A nine mile trail run at Kohler-Andrae State Park featuring beach, marsh and boardwalk sections, one midcourse aid station, post-run snacks, and awards for top finishers.

Timed ultrarunning at Lapham Peak State Park with 24, 12 and 6 hour options plus a distance division for marathon and longer targets. One mile loop, chip timing, an aid station, and a cupless refill policy.

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.

A monthlong October event with a virtual 99 kilometer challenge and in-person 2K, 5K and 10K trail races at SnowKraft Nordic, honoring lives lost to domestic violence and supporting survivors and local services.

A farm based obstacle course at Heim's Hillcrest Dairy in Algoma covers about 1.5 miles with tasks such as feeding calves and climbing over hay bales. Registration opens July 1 with an early price of $20 until September 1.

A fall trail event at Lapham Peak State Forest featuring timed 5K and 10K runs, accessible walk options, and a free 1K Smokey Bear run for children age 10 and under; participant shirts, awards, and post-event treats are included.

A community 5k and a 54 yard dash on October 4, 2026 in Glendale with an out-and-back course on the Oak Leaf Trail. Registration includes all-day entry to Milwaukee's Original Oktoberfest at Old Heidelberg Park.

Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.

Trail runs and a 1-mile walk at Fox Hill Nature Preserve on 10/11/2026, held to support conservation in the Cedar Lakes region; varied distances include 5K, 10K, a 1-mile walk, and a Kiddos 1K.

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.

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.