Trail Running calendar near St. Charles 2025-2026

The Kishwauketoe 5K Cross Country Run takes place in Williams Bay, Wisconsin, starting at the KNC entrance on Highway 67. The course features scenic grass trails through hills, woods, and prairie, offering a natural and challenging terrain for runners. The event includes a 5K run/walk and a children..

The Pinetum Mind Games Endurance Event, held at Lowell Park in Dixon, Illinois, is a unique running challenge featuring a 0.411-mile loop course through the pine tree upper loop area. Participants can choose from 6, 12, or 24-hour solo runs or three-person relays, starting on a Friday evening. The e..

The Jennie Hamilton Memorial 5 Mile Trail Run takes place at Stoney Run County Park in Hebron, Indiana. This trail race features a challenging 5-mile course marked with flags and arrows at major turns, including natural obstacles such as mud, bugs, and a pond crossing near the end, with a detour opt..

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 Oakadoke Trail Runs, held in Valparaiso, Indiana, is a summer trail running event featuring challenging courses through the scenic Creekside Trails. Participants can choose from three distances: 18 miles (two loops), 9 miles (one full loop), and 4 miles (half loop focusing on the Salt Creek sect..

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 hill climbs, and four creek cr..

The Chupacabra Endurance Run is a 10-hour endurance race held at Bluhm County Park in Westville, Indiana, as part of the Crazy Legs Race Series in 2025. Participants run multiple loops of a 3.4-3.5 mile trail with minimal pavement, completing each loop within one hour to avoid elimination. The event..

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..

The Cornell Days 5k and 1 Mile Fun Run/Walk is a family-friendly running event held in Cornell, Illinois, starting at Clinton Keith Mills Memorial Park. The race features an out-and-back course along the county blacktop roads through the scenic countryside, suitable for both first-time runners and e..

The Hobo Trail Runs, hosted by Rockford Road Runners, take place at Rock Cut State Park in Rockford, Illinois. This annual event offers multiple trail running distances including 10k, 25k, and 50k races, with options to participate in single races or the challenging Triple Crown series (85k total) o..

Dirt Circus - Chicago is a free community running event held in Crystal Lake, Illinois, celebrating local trail running and races. Organized by UltraSignup, this one-day festival features a social group run with options of 3 or 5 miles through scenic Veteran Acres Park. The event fosters camaraderie..

Timely Nonsense is a unique timed running event held in Chicago, IL, at a 58-acre park located at California and Montrose. Participants run a 0.75-mile paved loop for either 6 or 12 hours, with an aid station at the start/finish offering typical ultrarunning fare and additional vendor treats like ho..

The Tiger 10 Miler is an annual trail race held at Byron Forest Preserve and the Nardi Equine Prairie in Byron, Illinois. This 10-mile course features twists, turns, and hills, offering a challenging and scenic run through natural settings. Participants receive a custom finisher's medal, shirt, and..

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 featuring the lakefront and Northwestern University campus. The course combines paved paths and crushed gravel, offering beautiful views of the Chicago skyline. Runners share the..

The Tryon Farm 50k is a trail running event held at Tryon Farm in Michigan City, Indiana. The course features an 8-loop 4-mile circuit through a mix of open grassy fields, single-track dirt trails, and small pavement sections connecting different trail areas. The event also offers shorter distances..

The DIRWIN DASH, A Bearded Bash is a 5K run/walk event held annually in Waukesha, Wisconsin, at Fox River Park. This race honors the memory of Dave Irwin, a beloved guidance counselor and cross country enthusiast from Heritage Christian School. The course features a scenic trail through the woods, o..

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 Hennepin Hundred is a premier ultramarathon held in Sterling, Illinois, featuring 100-mile, 50-mile, 50K, and 100-mile team relay races. The point-to-point course follows the scenic, flat, and fast Hennepin Canal State Trail, Illinois’ longest multi-use trail, stretching from Sterling to Colona..

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..