Trail Running calendar near Whitewater 2025-2026

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 "Running Wild" Trail and Fun Run is held at the Rochelle Wildlife Conservation Club in Chana, Illinois. This family-friendly event features a challenging approximately 3-mile trail race on a double-loop course with hill climbs, rocky terrain, and possible mud, making it unsuitable for strollers...

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 the region. The event offers three race distances: 10K, half marathon (21K), and 50..

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 by completing one to three laps, or join a three-person relay team. The..

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 Summer Trail Classic is a trail running event held at Paul Douglas Forest Preserve in Hoffman Estates, Illinois. It offers three race distances: approximately 4 miles, 9.5 miles, and 13 miles, featuring twisting single-track trails that provide a true trail running experience. The event is part..

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, set for September 6, 2025. Participants can choose between a USATF-certified half marathon or 10K race, both featuring a flat and fast course that winds through the scenic Danada Forest Preserve on crushe..

Last Dot Standing is a unique endurance running event held at Belleville Community Park in Belleville, Wisconsin. Participants alternate running 4.2-mile legs between Belleville and Dot's Tavern, a historic local tavern, with one hour to complete each segment. The race continues hourly until only on..

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- or 12-hour ultra-running event held in Evanston, Illinois, along a scenic 2-mile loop on the lakefront path near Northwestern University. The course features a mix of paved and crushed gravel surfaces, offering beautiful views of the Chicago skyline and the north..

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 meadow paths, and 20% gravel, 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..

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, with the 5K covering the park's middle level and the 10K f..