Trail Running calendar near Janesville 2026-2027

Experience a natural trail run at Saw Wee Kee Park featuring a soft path with twists and turns. Complete this event to earn a piece of the 2026 series medal and enjoy seasonal swag in a beautiful outdoor setting.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

Trail races of about 5 and 10 miles through Veteran Acres and Sternes Woods in Crystal Lake, IL, with single-track trails, a cupless course, packet pickup options, and finisher medals for all distances.

An October trail run at the Black Hawk Unit of the Lower Wisconsin State Riverway, organized by volunteers. Proceeds support local conservation groups and the event posts results and photos after the run.

Experience a haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

Celebrate Halloween and support animal shelters at this dog friendly 5k in Busse Woods. Enjoy a flat paved course with treats for both humans and leashed pets at the finish line.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

Embrace an autumn adventure at the Big Timber XC Challenge, a trail run featuring a famous creek crossing through the woods of Camp Big Timber. Choose between a 3-mile or 5-mile course on grass and gravel paths. All runners get a shirt and..

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

A winter trail event at Governor Dodge State Park on Dec 5, 2026 offering 50K, 25K and 15K over horse trails, single and double track with multiple aid stations, cup-less hydration, and specific pacer and crewing rules for the 50K.

A four race winter trail series in Dixon, Illinois totaling 31 miles across four dates from December 2025 to March 2026. Distances range from 5K to 20K with series awards and age-category prizes.

A dog friendly trail running event at Lake Geneva Ziplines and Adventures with a 4 mile loop, an 8 mile option, and a focus on Canicross. Awards are reserved for teams running with dogs and all finishers receive a small gift.

Experience a unique winter obstacle course in Lake Geneva featuring distances from 5K to 20K. Enjoy a festival atmosphere with fire pits and food trucks after conquering challenges designed for both fun and competitive athletes.

Experience a unique 5K race held entirely on the frozen surface of Lake Mendota. Participants can run walk or skate across the ice while enjoying scenic views of downtown Madison and the university campus.

A winter trail ultrarun in Dousman, Wisconsin on Feb 27-28, 2027 offering 6, 12 and 24 hour solo or relay options, winter trail terrain, warming shelters, hot drinks and a post-race meal.