Trail Running calendar near Middleton 2025-2026

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

The Galena Sky Trail Races, set for May 17, 2025, offer an exciting challenge for trail running enthusiasts 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..

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 ultramarathon event held at Richard Bong State Recreation Area in Brighton, Wisconsin, on June 6, 2025. The event offers multiple race distances, including the Backyard Ultra and Backyard 24, catering to runners of all skill levels. Participants can enjoy scenic trails, rolling..

The Blue Mound Trail Run is an annual trail running event held at Blue Mound State Park in south central Wisconsin. Now in its 21st edition, the run offers two distance options: 10K and 18K. Organized by Wisconsin Trail Runs, a volunteer group, the event features scenic courses through the park’s na..

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 a scenic trail running event held in Whitewater, Wisconsin, along a portion of the iconic Ice Age Trail. This National Scenic Trail showcases the glacially sculpted landscape of the region. The event offers three race distances: 10K, half marathon (21K), and 50K, fe..

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 is a scenic running event held in Dubuque, Iowa, featuring 4-mile, 7-mile, and half marathon distances. The race takes place at the EB Lyons Nature Center and showcases challenging trails through the Mines of Spain park, including dirt single and double tracks, prairie..

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, tackling a scenic 2.25-mile loop with significant elevati..

Last Dot Standing is a unique ultramarathon event held in Belleville, Wisconsin, from September 19 to 22, 2025. Participants can compete in a last person standing race, running 4.2 miles to and from Dot's Tavern every hour until only one runner remains. The event also features 24-hour and 48-hour ra..

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 S'more Fun Trail Run is an exciting event taking place at Mirror Lake State Park, featuring a variety of races including a Mini-Marshmallow Mile for kids, a 5K Trail Walk, a 5K Trail Run, a 10K Trail Run, and a Half Marathon Trail Run. The event aims to promote the park and raise funds for ongoi..

The Trail Run at Indian Lake is an exciting running event held at Indian Lake County Park, featuring two course options: a long course of approximately 10.5 km and a short course of about 5.8 km. The event promotes sustainability by adopting a cup-free policy, encouraging participants to bring their..

The Lapham Peak Colorama Run/Walk is an annual fall running event held at Lapham Peak State Forest in Delafield, Wisconsin. Celebrating its 36th year in 2025, the event features 5K and 10K courses on wide, well-groomed ski and hiking trails. The 5K route tours the park's middle level, while the 10K..

Zachariah's Acres Fall Run, Walk & Roll is a charitable event taking place in Oconomowoc, WI, designed to support children with special needs. The event features a 5K, a half marathon, and a family-friendly walk and roll, all set against the backdrop of 125 acres of beautiful natural scenery. Partic..

The Mines of Spain 100 is an ultra-marathon event featuring both 100-mile and 100-kilometer races, set in the picturesque bluffs, prairies, and forests of eastern Iowa's Driftless region. The race course, approximately 20 miles long, offers a diverse range of terrains, including steep technical sing..

Soul Crusher is an exciting trail running event taking place in Crystal Lake, IL, featuring challenging 10-mile and 5-mile courses designed by Jeff Lenard. Known for its tough terrain, the race promises to test participants' limits, with a playful warning that it may "crush your soul." Runners can e..