Trail Running Calendar Wisconsin 2026-2027

Join this trail event at Minooka Park featuring half marathon 10K and 5K distances. Participants can choose between running walking and rucking on a scenic course with shaded trails and a notable hill challenge.

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.

Trail events at Rock River Heritage County Park on October 3, 2026 include a timed 5K with chip timing and a guided 2.4 mile walk, plus a park celebration with music, food trucks, tastings, and raffles.

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 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.

Two trail routes around Indian Lake County Park in Cross Plains, Wisconsin feature wetlands, forested slopes, and a section of the Ice Age Trail. The event is cup free and includes post-race music, food, and awards.

A community 2-mile cross country run/walk at Glacier Creek Middle School with in-person and virtual options, evening and race-day packet pickup, live electronic results, and awards; proceeds support course upkeep and the high school cross-c..

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.

Timed ultraruns in Southern Kettle Moraine Forest on Oct 10 to Oct 11, 2026. Solo runners or teams of up to four complete as many 3, 5, or 6 mile McMiller Trail loops as possible in 6, 12 or 20 hour formats.

A *10-mile* single-track trail race at Willow River State Park featuring technical wooded terrain, climbs, stairs, and a waterfall. The cupless course has an aid station at about 4.2 miles and on-site restrooms and parking.

Trail ultra at Bethel Horizons in the Driftless Area offering 50K, 20M and 10M looped courses with mixed singletrack, grassy ridgelines, rocky climbs, fully stocked aid stations and chip timing.

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.

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.

National Sweetest Day at Nashotah Park on October 17, 2026 offers running, walking, and ruck events from a kids 1K to a half marathon. Entry fees vary and several events include post race treats.

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.

An October trail run at the Black Hawk Unit of the Lower Wisconsin State Riverway, organized by volunteers. Proceeds support local conservation groups and the event posts results and photos after the run.

A daylong running event covering 50 miles through Door County, Wisconsin during peak fall color. Runners may compete solo or on teams of two to five, and the course has nine aid stations plus a post race buffet with drinks and pizza.