Trail Running calendar near Kankakee 2025-2026

Glazin' the Trail is a family-friendly run/walk event held at Kankakee Community College in Kankakee, Illinois. This donut-themed event features a 5K Donut Dash and a shorter 2K Sprinkle Sprint, both designed for participants of all ages, including children under 12 who can join for free. The course..

The Hickory Knolls Trail Run, held at Hickory Knolls Nature Area in St. Charles, Illinois, offers 5K and 10K individual races plus a 10K two-person relay. The course features a scenic, approximately 3-mile loop of grass, dirt, and gravel trails with a mix of flat sections and hills, set in a diverse..

The Trail Golf Endurance Challenge, held in Valparaiso, Indiana, is a unique trail running event featuring distances of 50K, 50K relay, 10 miles, and 10-mile relay. Unlike traditional races, it uses a golf-style scoring system where runners complete 3-4 mile "holes" each hour, aiming for the lowest..

The Jennie Hamilton Memorial 5 Mile Trail Run is held at Stoney Run County Park in Hebron, Indiana. This challenging trail race features a 5-mile course marked with flags and arrow signs at major turns. Runners may encounter mud, bugs, and a pond crossing near the end, with an optional detour adding..

The Oakadoke Trail Runs, held at Twin Creeks Farm in Valparaiso, Indiana, offer a scenic and challenging summer trail running experience. Participants can choose from 18-mile, 9-mile, or 4-mile distances, with courses featuring tree-covered single-track trails, winding switchbacks, farmland views, a..

The Chupacabra Endurance Run is a 10-hour endurance race held at Bluhm County Park in Westville, Indiana, as part of the Crazy Legs Race Series in 2025. Participants run multiple loops of a 3.4-3.5 mile trail with minimal pavement, completing each loop within one hour to avoid elimination. The event..

The Naperville Trails Half Marathon & 10K is an annual running event held in Wheaton, Illinois, at the scenic Danada Forest Preserve. Scheduled for September 6, 2025, the race offers both half marathon and 10K distances, including virtual options. The course is USATF certified, featuring a flat and..

The Kennekuk Road Runners - Wild Wild Wilderness is an annual running event held in Oakwood, Illinois, featuring a variety of races including a 5K, a 7.45-mile trail run, and the WWW Challenge. This event celebrates community spirit and resilience, welcoming both seasoned runners and newcomers. The..

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 ultra running fare and additional vendor treats like h..

Half Day at the Lake is a unique 6- and 12-hour ultramarathon held in Evanston, Illinois, along a scenic 2-mile loop on Chicago’s north shore lakefront path. The course features paved and crushed gravel surfaces, passing through Evanston’s lakefront and Northwestern University’s campus, offering bea..

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 circuit through a mix of open grassy fields, single-track dirt trails, and small pavement sections connecting different trail areas. The event also offers shorter distances..

The Fancy Nonsense 25K/50K is a whimsical ultramarathon held in the Palos Trail System near Willow Springs and Lemont, Illinois, about 20 minutes from downtown Chicago. Runners can choose from 25K, 50K, or 5-mile distances on a mostly single-track, 5.5-mile loop course that encourages joy and imagin..

The Forge Trail Run Festival, scheduled for November 15, 2025, in Lemont, IL, features a variety of trail running events including 10K, 20K (Half Marathon), 30K, and 60K races. Participants will navigate single and double-track trails through scenic woods and gravel paths around the historic Lemont..

The Bigfoot Half Trail Run is a half marathon trail race held at Stoney Run County Park in Hebron, Indiana. Participants complete the distance by running two loops around the park. The course features two aid stations: a manned station at the start/finish area and an unmanned station approximately 3..

The Cereal Killer 15k Trail Run takes place at Red Mill County Park in La Porte, Indiana. This trail race features a 15-kilometer course marked with flags and signs, consisting of four loops. Participants are advised to follow course markings carefully rather than other runners.The event offers a fu..

The Tombstone 50 Trail Run, part of the Crazy Legs Race Series, takes place at Sunset Hill Farm County Park in Valparaiso, Indiana. The event features three challenging distances: 30k, 50k, and a newly added 50-mile race, all on a new course with more hills, including the notable "Roller Coaster" hi..

False Spring Trail Runs, held in LaPorte, Indiana, offers challenging trail races on scenic, woodsy single-track paths featuring winding switchbacks and views of lakes and ponds. The event includes a 10K course—a single loop of well-established dirt trails—and a Half Marathon consisting of two laps,..

Childish Nonsense is a trail running event held in Palatine, Illinois, at Deer Grove Forest Preserve West. It offers multiple distances including a 50-mile, 50K, 25K, and 10K, with courses consisting of laps on a mostly wide, non-technical trail. Runners encounter a single aid station at the start/f..