Trail Running calendar near Shorewood 2025-2026

Naperville Trails Half Marathon & 10K is held in Wheaton, Illinois, with the start/finish at the DuPage County Forest Preserve District Headquarters. The event features Half Marathon and 10K distances along a flat, fast crushed limestone trail in the Danada Forest Preserve, finishing around a grass..

The Cornell Days 5k and 1 Mile Fun Run/Walk is a family-friendly event held at Clinton Keith Mills Memorial Park in Cornell, Illinois. The event takes place on Saturday, September 6, 2025. It offers two distances: a 5K and a 1 mile Fun Run/Walk, starting and finishing at the park along a county blac..

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 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 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..

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..

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..

Run The Woods is a charity running event held in Hudson, Illinois at Timber Pointe Outdoor Center (20 Timber Pointe Lane). The series includes 5K, 5K for Youth, 8K, 8K for Youth, and a 1 Mile Trail Walk – Untimed. While the site doesn’t describe a specific course layout, the venue suggests a family-..

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..

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..

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..

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..

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..

The Buckley 5 Miler is a scenic and challenging cross-country trail race held at the Buckley Homestead in Lowell, Indiana. The 5-mile course features a 2-mile loop on the north side of the park followed by a 3-mile loop through the park, finishing at the pioneer farm. Runners encounter a picturesque..

Palos Park Spooky Shuffle 2025 is a 5K and 10K trail run/walk held at Swallow Cliff South Forest Preserve in Palos Park, IL, organized by the Palos Park Department of Recreation & Parks in partnership with the Forest Preserves of Cook County. Runners traverse the Sag Valley Trail System on wide, unp..