Trail Running calendar near Waukesha 2026-2027

An 8K winter trail race at Oakhurst Forest Preserve on February 21, 2026. The course starts with a steep sledding hill and may include snow, ice, or mud, with finish-line water, snacks, and a finisher medal.

A four-race winter trail series around Rockford, Illinois, from Dec 20, 2025 to Mar 21, 2026. Distances range from 3 to 12 miles across local forest preserves, with a series entry option available.

The Zip Thaw is a canicross trail run on March 15, 2026, at Lake Geneva Ziplines. Choose a 4-mile or 8-mile loop on shared, wooded single-track. It's a dog-powered, cupless event with post-run refreshments.

A four-race winter trail series around Rockford, Illinois, from Dec 20, 2025 to Mar 21, 2026. Distances range from 3 to 12 miles across local forest preserves, with a series entry option available.

A 10K trail race at Hickory Knolls Discovery Center in St. Charles on March 22, 2026. Final event of a three race winter series with mixed terrain, finish line water and snacks, and finisher medals plus winter gear for series finishers.

Trailbreaker in Waukesha on March 29, 2026 offers marathon, half, 10K, 5K, walk, ruck events, a Kiddos 1K, and The RAD, with proceeds supporting the Park Foundation and courses on local trails including the Glacial Drumlin.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

A point to point trail run on the Northern Kettle Moraine Ice Age Trail near Greenbush, WI. Offers 25K and 50K distances with transportation to starts, aid stations, and a finish area with food and shelter.

Trail races on a 5 mile loop at Veterans Acres in Crystal Lake, IL offering 50K, 15 mile, and 5 mile options with one major aid station and age group awards. Registration closes April 10.

A looped trail race at Deer Grove Forest Preserve near Palatine, IL offering 10K, 25K, 50K and 50 mile options on soft gravel loops with a single aid station per lap and inclusive entry policies.

Three chip timed races in Belgium, WI on April 25, 2026: a flat moonlit 5k road course, a 10k hybrid with a trail section through Harrington Beach State Park, and a Lakeview half marathon with lake and rural scenery.

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.

A flat out and back half marathon and 10K along the limestone Great Western Trail on May 3, 2026, hosted by Fox River Trail Runners. Registration contributions support three local mental health charities.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

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..

Out and back trail races of 50 miles, 50K and half marathon on the Badger and Sugar River State Trails near Belleville, WI. Flat, soft rail trail with trestle bridges, scenic vistas and a 1/4 mile tunnel; generous cutoffs and aid stations.

Dirt Circus brings the trail running community together for a free festival in Crystal Lake. Enjoy a choice of group run distances, a vendor expo, food, and a raffle with prizes. Connect with local race directors and brands at this cupless,..

A multi-distance trail event near LaGrange, Wisconsin on June 13–14, 2026, featuring 100% trail courses and a lottery entry system. Distances range from 50K to 100 miles and the 100 mile finish in 30 hours qualifies for Western States.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

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.