Trail Running Calendar Illinois 2025-2026

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 Quail Ridge Farm Backyard Ultra will take place in Albion on Saturday 19 July 2025.

Madder Than a Wet Hen is a 5K running event held in Charleston, Illinois, at 17737 E County Road 380N. The race offers participants a scenic course through the local area, providing a community-focused atmosphere ideal for runners of all levels. The event takes place in July, promising summer weathe..

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 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, featuring twisting single-track trails that provide a true trail running experience. The event is part..

The Temptation 200 Ultras, held in Sand Ridge State Forest near 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. The course consists of multiple loops throu..

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

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 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..

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 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..

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..