Trail Running calendar near Williams Bay 2025-2026

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..

The Great Western Half-Marathon & 10K, organized by Fox River Trail Runners, is a popular race held annually on the scenic Great Western Trail. With a history spanning over 25 years, the event features a flat, out-and-back course that attracts runners of all levels. Participants can choose between t..

The F^3 Cap Sauers Trail Marathon & 10 Mile is set to take place in Palos Hills, IL, on May 10, 2025. This event features a challenging marathon and a 10-mile race, both traversing the scenic Cap Sauers Holding Nature Preserve, the largest undeveloped area in Cook County. Participants will experienc..

The Wildflower Run is an exciting running event taking place in Bristol, Wisconsin, featuring a 4.5-mile trail run and a 2-mile fun run/hike through the scenic Bristol Woods County Park. Scheduled for the third Saturday in May, the event coincides with peak wildflower viewing, making it a beautiful..

The Chicago 7-11 Hour Endurance Run, organized by Yeti Trail Runners, is a unique trail running event set in Willow Springs, IL. Participants can choose between a 7-hour or 11-hour endurance challenge, navigating a scenic 4-mile loop through the picturesque Wolf Road Woods and Palos Preserves. The e..

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 Hickory Knolls Trail Run, taking place on June 8, 2025, at the Hickory Knolls Discovery Center in St. Charles, IL, features a 5K, 10K, and a 10K relay event. Participants can enjoy a scenic course that includes grass and dirt trails, with a mix of flat sections and hills.The event is part of the..

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..

The Pinetum Mind Games Endurance Event is an exciting running challenge held at Lowell Park in Dixon, IL. Participants can choose to compete in 6, 12, or 24-hour formats, either solo or as part of a relay team. The course consists of a .411-mile loop designed to test mental and physical endurance, e..

The Chupacabra Trail Races, set in Dixon, IL, offers a unique night running experience on August 2, 2025. Participants can choose from various distances: 5 miles, 10 miles, 15 miles, or a 15-mile relay team option. The course features a mix of grass, gravel, and dirt, with a single track section.Run..

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..

The Gristmill Grind 10K is an annual trail race held at Franklin Creek State Parks Natural Area, known for its challenging terrain and scenic views. Scheduled for August 30, 2025, this event features a 10K race with significant elevation changes and creek crossings, as well as a 1-mile walk. Partici..

The Naperville Trails Half Marathon & 10K is a scenic running event taking place in Wheaton, Illinois, 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 Preserv..

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 of two or four. The race is set in a scenic 58-acre park, where runners will navigate a 0.75-mile paved loop.Ea..