Trail Running calendar near Oconomowoc 2025-2026

The NK50k is an annual trail running event held in Greenbush, Wisconsin, featuring a scenic point-to-point course along the Northern Kettle Moraine Ice Age Trail. Participants can expect a challenging 50K run, with aid stations providing water, sports drinks, and snacks throughout the course. The ev..

Run the Trailbreaker is an annual running event in Waukesha, Wisconsin, established in 1993. This community tradition features a variety of race distances, including a Marathon, Half-Marathon, 10K, 5K, and a Kiddos 1K, catering to runners of all levels. The event is organized by the Park Foundation..

The Sunset Safari 10k Trail Run is part of the 12th Annual Moonlight Meltdown event, taking place in Belgium, WI. This hybrid/crossover trail run offers participants a scenic experience through Harrington Beach State Park, featuring a 1.2-mile section on a snowmobile trail. The event is organized by..

Childish Nonsense is a whimsical running event taking place at Deer Grove Forest Preserve in Palatine, IL, featuring multiple race distances: 50 Miler, 50K, 25K, and 10K. The course consists of wide paths, making it accessible for participants of all levels. The event aims to foster a sense of commu..

The Earth Day 50K/15 Mile/5 Mile event, taking place in Crystal Lake, IL, offers participants a choice of three challenging race distances. Set in a scenic environment, the course features rolling hills and single-track trails, designed to provide an exhilarating experience for runners. The event pr..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an exciting endurance running event taking place in the scenic Kettle Moraine State Forest. Participants can choose from various race formats, including 6-hour, 12-hour, and 24-hour solo or relay options. The course features three unique loops of differ..

The Donald Dash Trail Run is an exciting running event taking place in Mount Horeb, Wisconsin, featuring two race distances: a 5K and a 15K. Designed to cater to both novice and experienced runners, the course includes a mix of prairie, single track, and hilly terrain. The event aims to promote comm..

Rumble on the Ridge is an exciting endurance event inspired by the Backyard Ultra format, taking place on a scenic family dairy farm in Arena, Wisconsin. Participants will tackle a looped course, known as "The Drifty Mile," which ranges from 1 to 1.25 miles with a minimum elevation gain of 250 feet...

The Sugar Badger 50/50 and Half is a scenic running event taking place in Belleville, Wisconsin, featuring a 50-mile, 50K, and half marathon distance. The race is set on the flat and soft rail trails of the Badger State Trail and the Sugar River State Trail, offering picturesque views, trestle bridg..

Bong Backyards is an exciting trail and ultra running event scheduled for June 6, 2025, at the Richard Bong State Recreation Area in Brighton, WI. This event caters to runners of all skill levels, offering multiple race distances, including the challenging Backyard Ultra and the shorter Backyard 24...

The Kettle Moraine 100 Endurance Races is a premier ultra marathon event held annually in June, featuring a variety of race distances including 100 miles, 100 kilometers, 50 kilometers, and 38 miles. Established in 1996, this trail race showcases the scenic beauty of the Kettle Moraine region, with..

The Sunburst 12 Hour Trail Festival, taking place on June 21, 2025, at Sunburst Ski Area in Kewaskum, WI, offers an exciting challenge for runners. Participants can choose between 6-hour and 12-hour solo events or join a relay team of three. The course features a mix of climbs and scenic trails, wit..

The Whitewater Trail Challenge is an exciting running event taking place on the scenic Ice Age Trail in Whitewater, Wisconsin. Scheduled for June 21, 2025, participants can choose from three distances: a 10K, a half marathon, and a 50K. The course features a mix of well-established trails and rollin..

The Dawn to Dusk Endurance Run is an exciting running event taking place at Camp Sinawa in Valders, WI, on June 28-29, 2025. Participants can choose from various race durations, including 24 hours, 15.5 hours, 8 hours, 6 hours, and a unique Dusk to Dawn challenge. The course features a 4.5-mile loop..

The Kishwauketoe 5K Cross Country Run is a community-focused running event taking place in Williams Bay, Wisconsin. Participants can choose between a 5K run/walk and a children's 1/4 mile walk/run for ages 10 and under. The course features scenic grass trails through hills, woods, and prairie, with..

Dances with Dirt Devil's Lake is an exciting trail running event set in the stunning landscape of Devil's Lake, Wisconsin, known for its unique geological features. Scheduled for July 12, 2025, this midsummer adventure offers various race distances, including 10K, half marathon, full marathon, 50K,..

The New Glarus Woods Trail Run is an annual event that celebrates outdoor fitness and community spirit, taking place in New Glarus, Wisconsin. This year marks the 6th edition of the run, which is part of the Savanna Trail Run Series. The event features multiple race options, including a 1 Mile Fun R..

Run the Hawk Trail Run is an exciting endurance event taking place at the historic Blackhawk Ski Club in Middleton, WI, on August 23, 2025. Participants can choose from various challenges, including 3, 6, and 12-hour solo runs or team relays, all set on a scenic 2.25-mile loop course featuring signi..

Last Dot Standing is a unique endurance running event taking place in Belleville, WI, from September 19 to 22, 2025. Participants will engage in a "last person standing" format, where they must run 4.2 miles to Dot's Tavern and back, with each leg of the race starting every hour on the hour. In addi..

Fallinline 125 is an exciting running event taking place in the scenic Kettle Moraine State Forest, Wisconsin. Participants will embark on a challenging 132-mile course that showcases the beauty of the Ice Age National Scenic Trail. The event aims to promote community engagement and environmental st..