Trail Running calendar near St. Charles 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..

Childish Nonsense is a whimsical running event taking place at Deer Grove Forest Preserve in Palatine, IL, featuring multiple race distances: 50 Miler, 50K, 25K, and 10K. The course consists of wide paths, making it accessible for participants of all levels. The event aims to foster a sense of commu..

The Earth Day 50K/15 Mile/5 Mile event, taking place in Crystal Lake, IL, offers participants a choice of three challenging race distances. Set in a scenic environment, the course features rolling hills and single-track trails, designed to provide an exhilarating experience for runners. The event pr..

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 Great Western Half-Marathon & 10K, organized by the Fox River Trail Runners, is a well-established running event held on the scenic Great Western Trail. Celebrating over 25 years, this competitive race features a flat, out-and-back course, making it accessible for runners of all levels. Schedule..

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, on May 17, 2025. 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..

Trail Run Xtreme is an exciting trail running event held in Portage, Indiana, featuring a challenging 12K trail race and a 3K kids race. Participants can expect a rugged course filled with roots, hills, and mud, designed to test their endurance and spirit. The event promotes camaraderie among runner..

Bong Backyards is an exciting trail and ultra running event scheduled for June 6, 2025, at the Richard Bong State Recreation Area in Brighton, WI. This event caters to runners of all skill levels, offering multiple race distances, including the challenging Backyard Ultra and the shorter Backyard 24...

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 an exciting running event that takes place along a scenic segment of the Ice Age Trail in Wisconsin, showcasing the stunning landscapes shaped by ancient glaciers. Participants can choose from three race distances: a 50K, a half marathon (21K), and a 10K, all design..

The Trail Golf Endurance Challenge is a unique trail running event that combines endurance racing with a golf-inspired scoring system. Participants can choose between a 50K, 50K Relay, 10M, or 10M Relay, with each route consisting of multiple "Holes" of approximately 3-4 miles. Runners aim to achiev..

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 Jennie Hamilton Memorial 5 Mile Trail Run is an exciting running event taking place at Stoney Run County Park in Hebron, Indiana. Organized by the Crazy Legs Race Series, this trail run emphasizes a fun and challenging experience in a natural setting. Participants can expect a well-marked course..

The Oakadoke Trail Runs is a summer trail running event held in Valparaiso, Indiana, featuring three race distances: 18 miles, 9 miles, and 4 miles. Participants will navigate scenic, tree-covered single-track trails with various elevations and challenging terrain, including multiple bridge crossing..

The Chupacabra Trail Races, set in Dixon, IL, offers an exciting night running experience on August 9, 2025. Participants can choose from three distances: 5 miles, 10 miles, or 15 miles, with a loop course that combines grass, gravel, and dirt trails. The event features a single aid station at the s..

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 for part..

The Chupacabra Endurance Run is a 10-hour race taking place at Bluhm County Park in Westville, Indiana, as part of the Crazy Legs Race Series in 2025. Participants will tackle a 3.4-3.5 mile loop, with the challenge of completing each loop within one hour to remain in the race. Runners can earn colo..