Trail Running calendar near Waukesha 2026-2027

Conclude the winter series with a 10K trail race at the Hickory Knolls Discovery Center. Navigate dirt paths and limestone trails to earn your finisher medal and final pieces of the challenge series gear.

Join a long-standing Waukesha tradition featuring marathon and shorter distances plus new rucking categories. Support local parks while enjoying a professionally managed event on scenic city trails.

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.

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..

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.

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.

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.

Test your discipline in this 6 hour trail challenge where you must complete a 5K every hour to stay in the race. Earn unique patches and medals while navigating the natural terrain of Deer Grove East.

Run a flat, out-and-back course on the historic Great Western Trail. Choose from a half-marathon or 10K distance. Your registration supports local mental health charities.

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.

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..

Experience the natural beauty of St. Charles at the Hickory Knolls Trail Run, featuring 5K, 10K, and relay options on scenic grass and dirt forest pathways.

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.

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.