Trail Running calendar near Naperville 2026-2027

Challenge yourself on the scenic, non-flat trails of Soldiers Memorial Park in LaPorte. Choose between a winding 10K loop or a two-lap Half Marathon, with festivities at the finish. The event supports youth runners and offers financial aid..

Event Overview Tour de Trails is a series of four winter trail runs held on Saturdays from December 2025 to March 2026. Each race is held at a different forest preserve or park in the Rockford, Illinois area. Participants can register for i..

Conclude the winter series with a 10K trail race at the Hickory Knolls Discovery Center. Navigate dirt paths and limestone trails to earn your finisher medal and final pieces of the challenge series gear.

Race against the clock on a 2.25-mile alternating loop trail in Lowell Park. Choose the 8-hour 806, the 3-hour 314, or form a relay team. Finishers within the time limit earn unique apparel.

Run for six hours on a 1.7-mile trail loop at Luhr County Park. See how many laps you can complete before time runs out. This timed event is organized by the inclusive Crazy Legs Race Series.

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.

Celebrate Earth Day on the trails at Veteran Acres park. Choose from a 50K, 15-mile, or 5-mile loop on scenic single-track. The event focuses on being landfill-free and offers awards for top finishers.

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 whimsical trail run in Deer Grove Forest Preserve featuring four distances on a wide, non-technical looped course. The event, organized by CUSS Running, includes inclusive community initiatives. One aid station at the start/finish support..

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.

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 the largest undeveloped nature preserve in Cook County on these wide horsetrail courses. Choose between a full marathon or a 10 mile run featuring significant elevation gains and a supportive two way traffic layout.

Experience the spring blooms at Bristol Woods County Park during this hilly trail run and hike. Support local environmental education while navigating scenic dirt paths through the Pringle Nature Center.

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.

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.

Join the free Dirt Circus community running festival in Crystal Lake on May 30, 2026. Choose between a 4.3-mile or 6.8-mile social group run, then enjoy a festival with food, an expo of local brands, and a raffle. Meet race directors and co..

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.