Trail Running calendar near Waukesha 2025-2026

ARKTOS is an ultra-running event taking place in Dousman, Wisconsin, from February 22 to 23, 2025. The event features various challenges, including 6-hour, 12-hour, and 20-hour races, available for both solo runners and relay teams of up to four participants. The race is capped at 160 runners, empha..

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 fun and challenging experience, with aid stations providing refreshments and support throughout the 50K distanc..

The Trailbreaker is an annual running event held in Waukesha, Wisconsin, since 1993, featuring a variety of races including a Marathon, Half Marathon, 10K, 5K, Walk, and a Kiddos 1K. Organized by the Park Foundation of Waukesha, the event serves as a fundraiser to enhance local parks and recreation..

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

The Earth Day 50K/15 Mile/5 Mile event, taking place in Crystal Lake, IL, offers runners a choice of three distances to celebrate Earth Day. The race features a scenic 5-mile loop course that includes single track and rolling hills, with a major aid station providing refreshments. Participants are e..

Childish Nonsense is a whimsical running event taking place at Deer Grove Forest Preserve in Palatine, IL. Participants can choose from various distances, including a 50 Miler, 50K, 25K, and 10K, all set on a wide, non-technical trail. The event aims to foster a sense of community and joy in ultraru..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an exciting long-distance running event taking place in the scenic Kettle Moraine State Forest. Participants can choose from various race formats, including a 6-hour, 12-hour, 24-hour solo, and a 4-person relay. The course features three unique loops of..

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 hills, providing a challenging yet enjoyable..

The Great Western Half-Marathon & 10K, organized by the Fox River Trail Runners, is a well-established running event held on the scenic Great Western Trail. Celebrating over 25 years, this competitive race features a flat, out-and-back course, making it accessible for runners of all levels. Schedule..

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 Whitewater Trail Challenge is an exciting running event taking place on June 21, 2025, in Whitewater, Wisconsin. Participants can choose from three race distances: a 10K, a half marathon (21K), and a 50K, all set against the stunning backdrop of the Ice Age Trail. This iconic trail spans 1,200 m..

The Sunburst 6 | 12 Hour Trail Festival is an exciting running event taking place at Sunburst Ski Area in Kewaskum, WI. Scheduled for June 21, 2025, participants can choose between solo or relay formats for 6 or 12 hours. Runners will navigate a challenging course featuring scenic trails and steep c..

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 an exciting running event taking place at the Kishwauketoe Nature Conservancy 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 h..

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 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 with significant elevation gain..

The Naperville Trails Half Marathon & 10K is a scenic running event taking place in Wheaton, IL, on September 6, 2025. Participants can choose between a half marathon and a newly introduced 10K distance, both of which traverse the beautiful crushed limestone trails of the Danada Forest Preserve. Thi..

Timely Nonsense is a unique running event taking place in Chicago, IL, featuring both 6-hour and 12-hour timed races. Participants can choose to run individually or as part of a relay team, with options for 2 or 4-person teams. The race is set in a scenic 58-acre park, where runners will navigate a..