Trail Running calendar near Oconomowoc 2026-2027

Zip Thaw is a spring canicross event on the scenic, wooded trails of Lake Geneva Ziplines and Adventures. Choose a 4 or 8 mile course to run with your dog using approved harness gear. Enjoy post run refreshments indoors and receive a finish..

Event Overview Tour de Trails is a series of four winter trail runs held on Saturdays from December 2025 to March 2026. Each race is held at a different forest preserve or park in the Rockford, Illinois area. Participants can register for i..

Experience a historic Waukesha tradition featuring a flat and scenic course through local parks and paved trails. With distances ranging from a kid friendly 1K to a full marathon, this event supports the local park system.

Event Details The NK50k is an annual fun run scheduled for April 11. It features 50K and 25K distances. The event is a point-to-point tour on the Ice Age Trail in the Northern Kettle Moraine State Forest, starting from the Ridge Road Trailh..

Celebrate Earth Day on the trails at Veteran Acres park. Choose from a 50K, 15-mile, or 5-mile loop on scenic single-track. The event focuses on being landfill-free and offers awards for top finishers.

A whimsical trail run in Deer Grove Forest Preserve featuring four distances on a wide, non-technical looped course. The event, organized by CUSS Running, includes inclusive community initiatives. One aid station at the start/finish support..

A trail race at Donald County Park in Mount Horeb on May 2, 2026, offering 5 km, 15 km and a Kids One Mile Fun Run; chip timing, aid stations, awards, and proceeds benefit Friends of Donald Park for trail maintenance.

The Conservation Chase is a trail running event at Lapham Peak State Park supporting local conservation. Choose from distances including a half marathon, 10K, 5K, and ruck or walk options. It's a cupless race with proceeds benefiting the Ta..

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.

Join the free Dirt Circus community running festival in Crystal Lake on May 30, 2026. Choose between a 4.3-mile or 6.8-mile social group run, then enjoy a festival with food, an expo of local brands, and a raffle. Meet race directors and co..

A trail run at Blue Mound State Park on June 6, 2026 offering 10K and 18K courses over varied single-track and ski trails; proceeds benefit the Friends of Blue Mound State Park.

Experience one of the oldest 100 mile races in the US on the scenic Ice Age Trail. This all-trail event offers distances from 38 miles to a 100 mile Western States qualifier in the heart of Wisconsin.

A trail running event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 10K, half marathon and 50K on rolling hills and well established trails.

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.

Event Overview The DWD Devil's Lake is a trail running event scheduled for July 11, 2026. It takes place at Devil's Lake, an area noted for its geological features formed in the ice age. The event is located in Baraboo, Wisconsin, just nort..

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.

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..