Trail Running calendar near St. Charles 2025-2026

The Run The Rails will take place in Elburn on Saturday 16 August 2025. You can run between 4 and 7 miles.

The Summer Trail Classic will take place in Hoffman Estates on Sunday 24 August 2025. You can run between 4 and 13 miles.

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 10-hour Run is held at Bluhm County Park in Westville, Indiana. This challenging event features a 3.4-3.5 mile trail loop with minimal pavement, which runners must complete within one hour per loop or face elimination. The race lasts 10 hours, testing endurance and speed, wi..

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 distance, both featuring a flat and fast course that winds through the scenic Danada Forest Preserve on cr..

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 culture. Organized by UltraSignup, the event features a festive atmosphere with a social run, food, raffle prizes, and an expo showcasing local races, run clubs, brands, and busine..

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 will take place in Byron on Saturday 20 September 2025. You can run 10 miles.

Half Day at the Lake is a unique ultra-running event held in Evanston, Illinois, featuring 6- and 12-hour race options. The race takes place on a scenic 2-mile loop along Chicago’s north shore lakefront path, passing through Evanston’s lakefront and Northwestern University’s campus. The course is a..

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 trail combining open grassy fields, single-track dirt trails, and small pavement sections. The event also offers shorter distances including 2-mile, 4-mile, 8-mile, and 25k..

The DIRWIN DASH, A Bearded Bash is a 5K run/walk event held annually at Fox River Park in Waukesha, Wisconsin, honoring the memory of Dave Irwin, a beloved guidance counselor and cross country enthusiast. The race features a scenic trail course through the woods, offering a refreshing alternative to..

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 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 the Rock River to t..

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 races on wide, well-groomed ski and hiking trails. The 5K course tours the park's middle level, while the 10K f..

The Fall Trail Classic - Marengo, IL will take place in Marengo on Saturday 4 October 2025. You can run between 4 and 7 miles.

The Autumn Leaf Run is a 5K trail race held at Oakdale Nature Preserve in Freeport, Illinois. Open to all ages and skill levels, the event offers a scenic course featuring diverse terrain such as wide tree-lined trails, moderate hills, prairie areas, bridge crossings, and single-track trail sections..

The Des Plaines River Trail Races, held in Lake County, Illinois, offer a scenic and fast trail running experience with distances including a Half Marathon, Marathon (Boston Qualifier), 50K, and 50 Mile ultra. Starting and finishing at Half Day Forest Preserve, the course features a flat, wide, crus..

The Wiglorious Day will take place in Delafield on Sunday 12 October 2025. You can run between 5 and 5 miles.