Trail Running calendar near Kankakee 2026-2027

Experience a 4 mile trail run through the historic St James Farm in Warrenville. Enjoy a scenic single loop course featuring rolling terrain, limestone paths, and wooded trails with awards for multiple age categories.

Fight for Air Climb at Prudential Plaza in Chicago is a stair climb event on April 12, 2026. It offers Full Route, Half Route, Team and Firefighter climb categories, each covering one mile.

Run through the scenic rolling trails of the Morton Arboretum on a USATF certified 10K course. Enjoy a lively post race party with live music and refreshments while supporting vital tree conservation and research.

A looped trail event at Deer Grove Forest Preserve in Palatine, IL offering 10K, 25K, 50K and 50 mile distances on mostly wide, non-technical trails with a single aid station at the start and finish.

Experience a bib timed run through the natural twists and turns of Saw Wee Kee Park. Join this spring event to earn a unique medal piece and enjoy the changing seasonal terrain in Yorkville.

Run or walk to support Anderson Humane at their largest fundraiser. Choose a timed 5K run or bring your dog for a 1.5-mile walk along the Batavia Riverwalk. The event includes awards, a lure course, and activities for animal lovers.

Camp Tecumseh’s tenth annual Running with Raccoons 5K takes place April 26, 2026 in Brookston, Indiana. This chip timed run/walk raises funds for the campership fund and follows a scenic route through camp grounds.

Experience the Three Ravines Course at Wolf Road Woods with distance options of 3.1 or 5.4 miles. This family friendly trail event features a mix of single track terrain and a post race celebration with craft brews.

Test your discipline in this 6 hour trail challenge where you must complete a 5K every hour to stay in the race. Earn unique patches and medals while navigating the natural terrain of Deer Grove East.

Run a flat, out-and-back course on the historic Great Western Trail. Choose from a half-marathon or 10K distance. Your registration supports local mental health charities.

Experience a scenic trail run through the Sag Valley Trail system with a marathon or 10 mile distance. Enjoy a non technical horse trail course followed by post race chili and beer at Teason’s Woods.

A backyard ultra in Wingate, IN on May 9, 2026 where runners repeat a 4 miles 880 feet out and back loop each hour on road, gravel and grass until one runner completes more loops than any other.

A trail race at Lake of the Woods Forest Preserve with an approximately 5 miles course through wooded trails and prairie. Organized by Second Wind Running Club with online registration through race day and proceeds supporting the Forest Pre..

A timed endurance trail event near Willow Springs on a 4 mile loop with single and double track, rolling hills, a signature aid station offering snacks and drinks, and a mandatory reusable cup policy.

Navigate the single track routes and wooded hills of the Outback Trail at Imagination Glen. This event features a 12K race and a 3K kids run through shaded terrain with mud and water crossings.

A chip timed 10K through mostly crushed limestone trails and wooded scenery at The Forge Lemont Quarries near Lemont, IL. Part of the Chicago Racing Circuit with overall and age group awards and a 450 runner capacity.

Experience an authentic trail run at Stoney Run County Park featuring a five mile course with an optional pond crossing. Celebrate Memorial Day with a traditional timed race and a post run gathering in Hebron.

Experience a seasonal trail run through the natural twists and turns of Saw Wee Kee Park. Complete this bib timed race to earn a piece of the 2026 series medal and enjoy the summer landscape.

This 5K run/walk takes place on the Rock Run Greenway Trail in Joliet, starting and ending at Cemeno's Pizza. All proceeds support local cancer patients through the Pat Clark Cancer Foundation. Registration includes a T-shirt and finisher m..

Experience the natural beauty of St. Charles at the Hickory Knolls Trail Run, featuring 5K, 10K, and relay options on scenic grass and dirt forest pathways.