Trail Running calendar near Cross Plains 2025-2026

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 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 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 Galena Sky Trail Races, set for May 17, 2025, offer an exciting challenge for trail runners at Chestnut Mountain Resort in Galena, IL. Participants can choose between an 8-hour or 4-hour timed loop course, featuring scenic views of the Mississippi River. The event includes a festive atmosphere w..

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..

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 Strawberry Solstice Run, organized by the Driftless Trail Collective, is set to take place on June 21, 2025, in Prairie du Chien, WI. This unique 10-hour overnight event features a 5.25-mile loop course, beginning at dusk and concluding at dawn. With a limit of 75 participants, the run aims to c..

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 Mines of Spain Trail Races, set in Dubuque, IA, 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 dir..

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..

The Tiger 10 Miler is an annual trail race held in Byron, Illinois, featuring a challenging 10-mile course through the scenic Byron Forest Preserve and Nardi Equine Prairie. Participants receive a custom finisher's medal, a race shirt, and have the chance to win awards in various age categories. The..

The Iowa Trail Run Series: Yellow River State Forest offers a unique running experience in the scenic driftless region of Iowa. Scheduled for September 21, 2025, this event features three race options: a 5K, a 10K, and a half marathon, catering to various skill levels. Participants can enjoy diverse..

The Swiss Valley Trail Races, set in the scenic Swiss Valley Nature Preserve in Peosta, IA, offers participants three challenging distances: 5.2 miles, 25K, and 50K. The course features rugged terrain, steep inclines, and creek crossings, making it a true test for trail runners. The event supports t..