Trail Running calendar near Sheboygan 2026-2027

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.

A farm-based cross country event at Scholl Farms in Montague, Michigan featuring 5K and 10K courses, a 1K kids race, a dog division, awards, potluck and optional tie-dyed shirts.

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..

Outagamie Stampede on June 27, 2026 combines a 5K cross-country run, a 4K barnyard obstacle course, and a 300 yard kids fun run at the Outagamie County Fair, with team and individual scoring and age group awards.

A prairie run and walk at Lapham Peak State Forest on July 11, 2026, using grass hiking and mountain bike trails. The event raises funds for prairie management and includes shirts for the first 100 participants and awards for winners.

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 late July trail weekend at Jazz Blueberry Farm featuring a 5K run walk, 10K run, 1 mile run and a 24 hour team relay with cross country style trails and onsite camping for relay teams.

Trail runs of 5K and 10K through pine forest and creek ridges in Whitehall, Michigan on July 25, 2026. The event includes a free kids run, award categories, a discounted pancake breakfast and festival activities.

A 10K walk/run on August 1, 2026, through the Nordic Trail System in Kettle Moraine State Forest with water refill stations, trail snacks, a cup-less policy, and donations supporting The Salvation Army.

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.

Trail races on August 29 and 30, 2026 offering 50 Mile, 50K, 26.2 Mile and 13.1 Mile distances. Registration is closed and a wait list will be available; organizers state the race includes notably large finisher medals.

Timed 24 hour, 12 hour and 6 hour runs take place at Lapham Peak State Park on September 5 and 6, 2026, on a one mile loop with night lighting and chip timing. The event includes a cupless aid station and a Distance division.

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.

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.

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.