Trail Running calendar near Whitewater 2025-2026

The Sugar Badger 50/50 and Half is a scenic running event held in Belleville, Wisconsin, featuring distances of 50 miles, 50 kilometers, and a half marathon. The race takes place on the flat, soft rail trails of the Badger State Trail and Sugar River State Trail, which include trestle bridges, sceni..

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, held at Hickory Knolls Nature Area in St. Charles, Illinois, offers 5K and 10K individual races plus a 10K two-person relay. The course features a scenic, approximately 3-mile loop of grass, dirt, and gravel trails with a mix of flat sections and hills, set in a diverse..

The Kettle Moraine 100 Endurance Trail Races, held annually in June in the Southern Kettles of Wisconsin, offer challenging ultra-distance events including 100-mile, 100k, 50k, and 38-mile races. Established in 1996, the course is predominantly trail-based, with about 65 miles running along the scen..

The Whitewater Trail Challenge, held in Whitewater, Wisconsin, is a scenic trail running event set along a portion of the iconic Ice Age Trail. This National Scenic Trail showcases the glacially sculpted landscape of Wisconsin with rolling hills and well-established trails. The event offers three ra..

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 Pinetum Mind Games Endurance Event, held at Lowell Park in Dixon, Illinois, is a unique endurance challenge featuring 6, 12, and 24-hour running or relay options. Participants run, walk, or crawl around a 0.411-mile loop known as the Pinetum, testing their mental toughness in a fun, supportive a..

The Chupacabra Trail Races take place in Dixon, Illinois, featuring night trail running on a 5-mile loop course composed of grass, gravel, dirt, and 30% single track. Participants can choose from distances of 5, 10, or 15 miles, or join a three-person relay team. The race starts just before sunset,..

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 takes place at the historic Blackhawk Ski Club in Middleton, Wisconsin. This endurance event features 3, 6, and 12-hour challenges where participants complete as many laps as possible on a scenic 2.25-mile loop with 345 feet of elevation gain per lap. The course includes diver..

The Gristmill Grind 10K is a challenging trail race held annually at Franklin Creek State Park in Franklin Grove, Illinois. Known as one of the most difficult 10Ks in the area, the course features technical trails with approximately 800 feet of elevation gain, multiple hills, and four creek crossing..

The Naperville Trails Half Marathon & 10K is an annual running event held in Wheaton, Illinois, at the scenic Danada Forest Preserve. Scheduled for September 6, 2025, the race offers both half marathon and 10K distances, including virtual options. The course is USATF certified, featuring a flat and..

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 Fallinline 125 is an ultramarathon event held in Greenbush, Wisconsin, covering approximately 132 miles through the scenic Kettle Moraine State Forest along the Ice Age National Scenic Trail. The course traverses the Northern, Middle, and Southern Kettle units, featuring a mix of rugged single-t..

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..

Half Day at the Lake is a unique 6- and 12-hour ultramarathon held in Evanston, Illinois, along a scenic 2-mile loop on Chicago’s north shore lakefront path. The course features paved and crushed gravel surfaces, passing through Evanston’s lakefront and Northwestern University’s campus, offering bea..

Hindsight Ultra Trail Runs, held in Dixon, Illinois, offers a grassroots ultra running experience with distances of 25K, 50K, 100K, and 100 miles. The course features a 7.85-mile loop combining roughly 50% singletrack, 30% grassy meadows, and 20% gravel paths, with about 6,200 feet of elevation gain..

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..