Trail Running calendar near St. Charles 2025-2026

Dirt Circus Chicago is a one-day, free community trail-running festival in the Chicago area, organized by UltraSignup. The event blends a casual social run with a pop-up expo featuring local race directors, brands, shops, and coaches. Participants choose between two routes, approximately 4.5 miles o..

Timely Nonsense is an urban ultramarathon held at a 58-acre park in Chicago, at the intersection of California and Montrose. The course features a 0.75-mile paved loop that runners complete for the 6-hour or 12-hour timed events. An aid station at the Start/Finish provides typical ultrarunning fare,..

The Tiger 10 Miler is an annual trail race held at Byron Forest Preserve and the Nardi Equine Prairie in Byron, Illinois. The 8th edition of this event features a challenging 10-mile course with twists, turns, and hills through scenic natural areas. Participants receive a custom finisher's medal and..

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 trail runs take place on September 20, 2025, at Tryon Farm in Michigan City, Indiana. Distances offered include: 2 mile Fun Run/Walk 4 mile trail run 8 mile trail run 25k trail run 50k trail run The event benefits the Tryon Farm Institute and is presented by the Crazy Legs Race Ser..

Limestone Rocks! 8-Hour or 4-Hour Race takes place at Limestone Park in Kankakee, Illinois. Runners choose an endurance 8-Hour or a 4-Hour option, competing on a 1.65-mile loop course. The surface is mostly crushed limestone with sections of asphalt; the course is roughly half flat and half hilly, f..

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..

Bloomingdale Trail 5K is an annual, family-friendly running event in Chicago, Illinois. The day features a timed 5K race along with ¼- and ½-mile dashes for young runners. The event location is 1834 N Lawndale Ave, Chicago, IL 60647, and the site describes a welcoming atmosphere for runners of all a..

Anderson Humane's Walk4Animals & 5K Run takes place in Batavia, Illinois, centered at the Peg Bond Center at 100 N Island Ave along the Batavia Riverwalk. The event offers a 5K Run (timed), a 1.5-mile Walk, and a T-Shirt Only option. The Walk4Animals route is a 1.65-mile loop around the Batavia Rive..

The Fall Trail Classic 2.0 is a trail running event held at Marengo Ridge Conservation Area in Marengo, Illinois. It features two races on the same day: a 4-mile run through oak and hickory woodlands, small stream bridges, and restored prairie trails, and a 7-mile run that includes the 4-mile loop p..

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..

October 4-5, 2025, The Hennepin Hundred is Illinois’ only point-to-point, all-trail ultramarathon, running from Sterling along the Rock River to Colona near the Mississippi and following the 104-mile Hennepin Canal State Trail through northwest Illinois’ historic locks, lift bridges, and scenic farm..

Autumn Leaf Run is a 5K trail race held in Freeport, Illinois, at Oakdale Nature Preserve. The course loops through diverse terrain, including wide tree-lined trails, moderate hills, prairie areas, bridge crossings, and several single-track sections. The start and finish are in close proximity, and..

Fire Zone 5k is a first-time event hosted by the Lockport Fire Foundation in Lockport, Illinois. The 5k takes place on a Forest Preserve trail, with a single full marked loop starting at the Hassert Park parking lot across from Lockport Township Fire Station Six and ending back there. Runners and wa..

Farmer Ken's Pumpkin Dash 5K takes place in Franksville, Wisconsin (53126). It is a 5K trail run along a grass/dirt path set beside corn and other farm fields, offering a scenic rural landscape. The course runs through agricultural surroundings, giving runners a scenic, rustic experience.Participant..

Des Plaines River Trail Races is an endurance trail event held in Lake County, Illinois, starting and finishing at Half Day Forest Preserve. The program features a Half Marathon, Marathon (Boston Qualifier), 50K, and 50 Mile ultra. Runners traverse a 100% trail course on a fast, flat crushed gravel..

Wiglorious Day is a Southern Kettle Duathlon held at Lapham Peak State Park in Delafield, Wisconsin. The event includes three distances: a 5-mile run, a 5-mile bike, and a final 5-mile run, with options for solo competition or 2- or 3-person relays (Soulo, or teams). The run takes place on wide, gro..

Soul Crusher is a trail-running event in Crystal Lake, Illinois, offering 5- and 10-mile options. Runners navigate single-track forest trails through Veteran Acres and Sternes Woods, with a course described as challenging, fun, and bone-decorated. The start line sits in the middle of the park at a s..

Saw Wee Kee - Fall Trail Run is held at Saw Wee Kee Park, Sundown Lane, Yorkville, Illinois. The event is the Fall Trail Run segment of a four-race series; each race features a different course and medal piece, and completing all four earns the series medal with different seasonal swag at each stop...