Trail Running calendar near Kankakee 2025-2026

Warm up your winter running at the Frozen Feet 5k Trail Run on January 3 at Creek Ridge County Park. Enjoy two chilly looped trails with a few hills, grab a free winter hat and gloves, and refuel with snacks and drinks after the finish.

Run the Kennekuk Road Runners Siberian Express, a 7.45 mile winter trail through Kickapoo State Park with steep climbs, creek crossings and wildlife. First 150 finishers receive awards and post race festivities are at Vermilion Brewing.

Tackle the Fox Valley Winter Challenge 5K at Dick Young Forest Preserve, the first of a three race trail series that may feature snow, slush or mud. Finishers get a medal and single race entrants receive a cozy winter hat.

Chill out and race the Frozen Tundra IPA 5K along the Des Plaines River Trail in Lincolnshire, then warm up at a lively post race party at Half Day Brewing with beer, food and prizes. Limited to 300 spots so register early.

Run the Cereal Killer 15K at Red Mill County Park on February 7, 2026 with four scenic loops, cereal stations and Deathwish Coffee. All finishers get a limited edition long sleeve shirt or winter hat and gloves while supplies last.

Yeti Trail Half at Bluhm County Park in Westville, IN offers a rugged half on four rooty single track loops for trail lovers. Participants get a limited edition long sleeve shirt and winter hat and gloves while supplies last.

Run the Fox Valley Winter Challenge Trail Series 8K in Aurora on Feb 21, the middle race on a scenic but wintry trail with woods, open paths and possible snow or mud. All finishers get a medal and single race participants receive a cozy win..

Hit the wooded trails at Sunset Hill County Park for the Foot Pursuit 5K, a scenic 3.1 mile run or walk across rolling hills. Enjoy friendly competition, age group awards, and postrace camaraderie in Valparaiso.

Tombstone at Sunset Hill Farm County Park on March 14, 2026 offers 30k, 50k and a new 50 mile on a hillier course with a Roller Coaster section. Expect aid, limited event swag and distinctive finisher awards.

Get muddy on wooded single and double track through the historic Lemont Quarries at Muddy Shamrock at The Forge with a half marathon or quarter marathon. Expect rugged terrain, chip timing, awards, a tee and a lively post race party.

Experience the False Spring Trail Runs in LaPorte, Indiana on March 21, 2026, with scenic single track, winding switchbacks, and lakeside views. Pick a 10K or a two loop half marathon, tackle rolling hills, and unwind at lively post race fe..

Wrap up winter on scenic mixed trails at the Fox Valley Winter Challenge 10K in St. Charles on March 22, 2026. Expect varied footing, a finisher medal and cozy winter hat, plus bundle pricing if you tackled other series races.

Chauncey’s 4 at The Farm is a friendly spring trail run at St James Farm in Winfield, IL, featuring a scenic 4 mile loop over limestone and wooded paths. Join the Dick Pond Trail Race Series and earn a collectible finisher woodallion.

Save the Drama for your Llama is a six hour trail run at Luhr County Park on April 4, 2026, where runners complete 1.7 mile loops to see who covers the most distance. Fun, low key and perfect for trail lovers of all paces.

Childish Nonsense is a playful trail run at Deer Grove in Palatine offering distances from 10K to 50 miles on mostly smooth looped trails. Expect laps, an on course aid station, and plenty of shenanigans from the whimsical organizers.

Run the Great Western Half Marathon and 10K on a flat out and back limestone path along the historic Great Western Trail. Hosted by Fox River Trail Runners, this longtime race supports local mental health charities.

Run scenic horse and forest trails at Teason's Woods on May 9, 2026 with a 26.2 mile marathon or a 10 mile option. Finishers get a wooden medal and can refuel with hot chili and beer.

Join the JH Memorial 5 Mile Trail Run on May 25, 2026 at Stoney Run County Park in Hebron IN for a scenic, rugged 5 mile on park trails. Expect mud, a possible pond crossing with detour, and postrace refreshments.

Celebrate the 25th anniversary 5K for Double "J" in Joliet on June 6, 2026 as participants run the Rock Run Greenway and finish at Cemeno's. Proceeds support the Pat Clark Cancer Foundation and registration includes a T shirt and medal.

Join the 28th annual Lake Mingo Trail Run on June 13, 2026 at Kennekuk Cove County Park, a scenic 7.1 mile loop mostly on natural trails with rolling hills and nine bridges. Celebrate afterward with food, beer, and great trail camaraderie.