Trail Running Calendar Illinois 2025-2026

The Madder Than a Wet Hen 5K is a unique summer trail race held in Charleston, Illinois, at Willenborg Woods. This challenging 5K features about 1,100 feet of elevation gain and includes a memorable one-third mile stretch running directly through the shallow Embarras River, offering a wet and wild e..

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..

Run the Rails is a community running event held in Elburn, Illinois, featuring a 4-mile run, a 7-mile run, and a 1-mile fun run. Presented by the Elburn Parks Commission, the race offers a vibrant atmosphere with opportunities for local businesses to sponsor and gain visibility through banners, race..

The Shawnee Hills Trail Races, held at Camp Ondessonk in Ozark, Illinois, offer challenging ultramarathon distances including 100 miles, 100K, 50K, and a half marathon. Set within the scenic Shawnee National Forest, the course features a figure-eight loop with 80% single-track trails, technical terr..

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, providing a true trail running experience on twisting single-track trails. The event is part of the 202..

The Temptation 200 Ultras, held annually at Sand Ridge State Forest in Forest City, Illinois, is a challenging ultramarathon event celebrating its 7th anniversary in 2025. The race offers multiple distances: a grueling 200K, a 50K, and a "Not At All Tempted" 10K, all set on a demanding forest course..

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 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 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 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..

The Wild Wild Wilderness is an annual running event held at Kickapoo State Recreation Area in Oakwood, Illinois. Established in 1981, the race features multiple distances including a 5K, a challenging 7.45-mile trail run, and a combined WWW Challenge. The 7.45-mile course is predominantly trail-base..

The Last Boyscout is a challenging Last Man Standing race held at Ferne Clyffe State Park in Goreville, Illinois. Participants run a 4.167-mile loop on the Boyscout Trail, featuring single track, jeep roads, paved sections, and about 600 feet of elevation gain per loop. The race tests endurance and..

The Timely Nonsense - Chicago, IL will take place in Chicago on Sunday 14 September 2025.

The Big Horse Vineyards 5K, hosted by Gut Check Fitness in Lewistown, Illinois, is a unique trail and mud run featuring natural obstacles such as hills, hollers, streams, ponds, and an epic slip-n-slide. This challenging yet fun course encourages participants of all ages and abilities to keep pushin..

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..

The 4sta Hike is an annual trail running event held at Loud Thunder Forest Preserve near Andalusia, Illinois, along the Mississippi River. Participants run a challenging 1-mile loop featuring smooth single track, rocks, roots, downed trees, and steep gradients up to 48%. The course offers two option..

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..

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 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..