Trail Running calendar near Middleton 2025-2026

The Frozen Assets 5K Run/Walk, organized by Clean Lakes Alliance, invites participants to experience a unique running event on the frozen surface of Lake Mendota in Madison, Wisconsin. This event features both a chip-timed 5K and an untimed walk, allowing individuals of all ages to join in the fun...

The Tour de Trails is an exciting running event organized by the Rockford Road Runners, featuring both a 9-mile and a 12-mile race. Scheduled for February and March 2025, this event invites runners of all levels to experience the scenic trails of Rockford. Participants can enjoy a well-organized rac..

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. With a cap of 160 runners, the race is e..

The Bald Unyielding Twilight Trail Trial is an exciting ultra-running event taking place in Mount Morris, Illinois, featuring timed races of 3, 6, and 12 hours. Scheduled for February 22-23, 2025, this unique nighttime challenge allows participants to test their endurance and night gear on a scenic..

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 Tour de Dodge is an annual trail running event organized by the Driftless Trail Collective, taking place at Governor Dodge State Park in Dodgeville, WI. Scheduled for April 19, 2025, the event features three race distances: 50K, 27K, and 10K, with varying elevation gains and aid stations along t..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an exciting long-distance running event taking place in Dousman, Wisconsin, featuring various race options including 6-hour, 12-hour, and 24-hour solo and relay formats. Participants can choose from three unique loops of different lengths, allowing for..

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..

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 navigate a looped course, known as "The Drifty Mile," which varies between 1 to 1.25 miles with a minimum elevation gain of 250..

The Galena Sky Trail Races, taking place at Chestnut Mountain Resort in Galena, IL, features an 8-hour and a 4-hour timed loop course, offering runners a chance to enjoy scenic views of the Mississippi River while navigating challenging trails. Participants can run as many loops as possible within t..

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 State Forest,..

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, and a 50K, all set against the stunning backdrop of the Ice Age Trail, a 1,200-mile scenic footpath. The cou..

The Sunburst 12 Hour Trail Festival, taking place on June 21, 2025, at Sunburst Ski Area in Kewaskum, WI, offers both 6 and 12-hour solo and relay running events. Participants will navigate a challenging course featuring scenic trails and significant elevation changes. Runners will receive a golden..

The Kishwauketoe 5K Cross Country Run is an exciting running event taking place at the Kishwauketoe Nature Conservancy in Williams Bay, Wisconsin. The event features a 5K run/walk and a children's 1/4 mile walk/run, making it accessible for participants of all ages. The course winds through scenic g..

Dances with Dirt Devil's Lake is an exciting midsummer trail running event set in the stunning landscape of Devil's Lake, Wisconsin. Participants can choose from various distances, including 10K, half marathon (13.1M), full marathon (26.2M), 50K, and 50M. The event features a marked course with aid..

The Mines of Spain Trail Races, set in Dubuque, Iowa, offers a thrilling experience for runners of all levels with distances of 4 miles, 7 miles, and a half marathon. Participants will navigate through the scenic and challenging trails of the Mines of Spain, featuring diverse terrain that includes d..

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 Last Dot Standing event, hosted by Ten Junk Miles, takes place from September 19 to 22, 2025, in Belleville, WI. This unique running challenge requires participants to alternate between running 4.2 miles to Dot's Tavern and back, with a one-hour time limit for each leg. The event continues until..