Trail Running calendar near Sheboygan 2026-2027

An ultrarunning event in Kettle Moraine State Forest on May 2–3, 2026 offering 6 hour, 12 hour and 24 hour solo and relay formats across three loop lengths. Jackpot cash prizes are funded from registration fees and distributed to top finish..

A long running Wisconsin trail ultramarathon that winds through forests, rocky ridges and glacial landforms. The event offers 50 miles, 50K and a half marathon and typically sells out quickly.

A low-impact, no-frills running event in Delafield, WI that highlights Lapham Peak State Park and raises funds for Tall Pines Conservancy. Races range from a Half Marathon to a free kids 1K.

Experience an off road cross country style event at the PM Conservation Park in Ludington. This 5k run or walk is open to all ages and abilities with prizes for various age groups and master categories.

A community trail run and walk on June 13, 2026 at Crossroads at Big Creek Nature Preserve offering 2K, 5K and 10K options with chip timing, aid stations, participant trees, and locally sourced prizes.

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.

Multi distance endurance event at Camp Sinawa near Valders, WI offering 24 hour, 15.5 hour, 8 hour, 6 hour and dusk to dawn formats on a 4.5 mile loop with 330 ft gain per lap.

A prairie trail run and walk at Lapham Peak State Forest on July 11, 2026 that raises funds for prairie management, offers awards and shirts for early participants, and includes merchandise, seed sales and on-site food.

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..

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.

Experience a cross country trail run through the fields of Jazz Blueberry Farm in Shelby. Choose between 10k, 5k, and 1 mile distances before enjoying the opportunity to pick fresh blueberries on site.

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.

Thanks Sandy is a *9 mile* trail run at Kohler-Andrae State Park near Sheboygan, WI, featuring beach, marsh and cordwalk sections, a three hour cutoff, one on-course aid station and post-run snacks with dietary options.

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.

Take on a scenic one mile loop at Lapham Peak with 24, 12, and 6 hour timed options or set distance goals like a marathon or 50 miles. Lighted night laps, a stocked aid station, and a welcoming club vibe make every lap count.

Trail marathon and half marathon at High Cliff State Park featuring technical singletrack, prairie sections and Lake Winnebago views. The event is cupless with aid stations and proceeds supporting the park.

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.

An annual October run and walk at Lapham Peak with 5K and 10K distances plus a Smokey Bear Fun Run. Proceeds support Lapham Peak projects and past editions publish official race results.

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.