Trail Running calendar near West Bend 2026-2027

Trailbreaker in Waukesha offers distances from a marathon to a kids 1K and new 2026 ruck events. The event supports the Park Foundation, which has reinvested over $200,000 in local parks and recreation.

Experience a seven month trail adventure through the scenic parks of Waukesha County. Choose from running, walking, or rucking across distances ranging from 5K to a Half Marathon.

A point to point trail run on the Northern Kettle Moraine Ice Age Trail in Greenbush, WI, offering 25K and 50K options, transport from the finish to starts, aid stations, drop bag access, and post run food.

Experience a unique chip timed race in Belgium featuring road and trail sections through Harrington Beach State Park. Choose between a fast 5k road course, a 10k hybrid trail run, or a scenic half marathon with Lake Michigan views.

Experience an illuminated night obstacle race in Mchenry featuring torch lit trails and technical rigs. Participants can enjoy live entertainment and bonfires after completing their 5k or unlimited lap challenge.

A low-impact trail event at Lapham Peak Park offering distances from a Kiddos 1K to a half marathon, with ruck and walk options, cupless aid stations, and proceeds benefiting Tall Pines Conservancy.

Experience the spring blooms at Bristol Woods County Park during this hilly trail run and hike. Support local environmental education while navigating scenic dirt paths through the Pringle Nature Center.

The Sugar Badger 50 Miles is a trail ultramarathon scheduled for May 2026. Organized by Ten Junk Miles Racing, it focuses on a community atmosphere on the trails. The event is a single 50-mile distance challenge.

An annual trail ultra held each June with 100 mile, 100k, 50k and 38 mile options; much of the course runs on the Ice Age Trail. Registration for 2026 is by Ultrasignup lottery with a waitlist and early-invite options.

Experience the glacial landscapes of Wisconsin at the Whitewater Trail Challenge. Run along the historic Ice Age Trail with 10K, Half Marathon, and 50K distances starting from the scenic Rice Lake Nature Trail.

The Dawn to Dusk Endurance Run takes place on the trails of Camp Sinawa in Valders, Wisconsin. Runners can choose from multiple timed events on a challenging 4.5-mile loop with varied terrain.

This cross country run on July 4th in Williams Bay offers a 5K on grass trails through the Kishwauketoe Nature Conservancy. A kids' quarter-mile event is also available. Registration is online only, with awards for top age-group finishers.

Experience the Savage Race in Spring Grove with obstacles and mud across multiple distances. Choose between a five to seven mile course or the shorter three mile Blitz for an engaging outdoor fitness experience.

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.

Take on the Cliff Runner 10K on July 19, 2026 at High Cliff State Park, a rugged singletrack course with rocks, roots and steep climbs. Registration includes a Cliff Runner tee and finisher medal, with proceeds to Purdy Nature Preserve.

This 10k walk/run explores the trails of Kettle Moraine State Forest in Wisconsin. It's a cup-less event with water refills and snacks provided. A portion of donations supports The Salvation Army.

Thanks Sandy is a 9 mile trail run through the scenic Kohler-Andrae State Park in Wisconsin. With a flat course along Lake Michigan and a boardwalk section, it offers a unique evening race. All finishers receive a commemorative token.

Experience a Scottish themed obstacle course race in Pingree Grove featuring 15k, 5k, and family 3k distances. Challenges include classic rigs and unique tasks like archery and caber carries in a Highland setting.

This annual community event in Sun Prairie features a 5k race and a kids' fun run, with a course on neighborhood bike paths. Proceeds go directly to support the local high school cross country team.

Run the Hawk offers timed trail challenges on a scenic 2.25-mile loop at Wisconsin's Blackhawk Ski Club. Choose from 3, 6, or 12-hour solo or relay events, or a shorter 1.7-mile fun run. The event features unique course landmarks, team tent..