Trail Running calendar near Whitewater 2026-2027

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 4 mile trail run through the historic St James Farm in Warrenville. Enjoy a scenic single loop course featuring rolling terrain, limestone paths, and wooded trails with awards for multiple age categories.

Trail race at Veterans Acres in Crystal Lake on April 18, 2026 offering 50K, 15 Mile, and 5 Mile options on a 5-mile single-track loop with one main aid station and an eight-hour cutoff.

Run through the scenic rolling trails of the Morton Arboretum on a USATF certified 10K course. Enjoy a lively post race party with live music and refreshments while supporting vital tree conservation and research.

Childish Nonsense is a lap based trail event at Deer Grove Forest Preserve in Palatine, IL offering 10K, 25K, 50K and 50 mile distances with a mostly wide path course and a single aid station every 5.5 miles.

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.

Run or walk to support Anderson Humane at their largest fundraiser. Choose a timed 5K run or bring your dog for a 1.5-mile walk along the Batavia Riverwalk. The event includes awards, a lure course, and activities for animal lovers.

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 classic Midwest ultra on varied glacial terrain offering 50-mile, 50K and half-marathon options with scheduled training runs, a strict no-transfer policy and on-site medical support.

A Last Person Standing backyard ultra on a private farm near Arena, Wisconsin, where runners repeat a 1.0 to 1.25 mile loop every 20 minutes until one remains. The field is capped at 75 and a waitlist is used if it fills.

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.

Flat out-and-back rail-trail races near Belleville, WI on May 23, 2026 offering 50 miles, 50K, and a half marathon, with aid stations, event swag, free food and drinks, and a tunnel and trestle-bridge scenery.

Test your grit at Byron Motosports Park with tactical obstacle courses ranging from 5K to 10K endurance laps. Choose from elite vest challenges, weighted rucking, or open waves designed to honor the resilience of first responders.

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.