Trail Running calendar near Naperville 2026-2027

A 3.1 mile all-trail run at Sunset Hill County Park in Valparaiso on March 7, 2026, with age group and overall awards, guaranteed shirts for early registrants, and a Police Fire Criminal Justice department challenge.

Event Overview The Tombstone Trail Run takes place on March 14, 2026 at Sunset Hill Farm County Park in Valparaiso, Indiana. The event offers three trail running distances: a 30k, a 50k, and a new 50-mile distance added for 2026. Course &am..

Hit the trails at The Forge for the Muddy Shamrock races. Choose between a half marathon or quarter marathon on wooded, adventurous paths near the Lemont Quarries. Enjoy chip timing and a post-race celebration.

Zip Thaw is a spring canicross event on the scenic, wooded trails of Lake Geneva Ziplines and Adventures. Choose a 4 or 8 mile course to run with your dog using approved harness gear. Enjoy post run refreshments indoors and receive a finish..

Event Overview The False Spring Trail Runs take place on Saturday, March 21, 2026, at Soldiers Memorial Park in LaPorte, Indiana. The event offers two distances: a Half Marathon and a 10K race. The course uses established dirt trails, descr..

A four-race winter trail series around Rockford, Illinois, from Dec 20, 2025 to Mar 21, 2026. Distances range from 3 to 12 miles across local forest preserves, with a series entry option available.

A 10K trail race at Hickory Knolls Discovery Center in St. Charles on March 22, 2026. Final event of a three race winter series with mixed terrain, finish line water and snacks, and finisher medals plus winter gear for series finishers.

Timed loop trail races at Lowell Park in Dixon, IL include 33.75-mile and 13.5-mile options plus a relay. Single track loops alternate direction each lap and a staffed aid station provides drinks and snacks.

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.

Hit the trails for Chauncey's 4 at The Farm, a 4-mile stampede through the historic St James Farm. It's the kick-off event for the 2026 trail running series. Runners can tackle the rolling limestone and wooded paths for a chance at awards a..

Trail races on a 5 mile loop at Veterans Acres in Crystal Lake, IL offering 50K, 15 mile, and 5 mile options with one major aid station and age group awards. Registration closes April 10.

Run a USATF certified 10K through the scenic Morton Arboretum. Celebrate at a post race party with live music and refreshments. A fundraising option supports the arboretum's mission.

A looped trail race at Deer Grove Forest Preserve near Palatine, IL offering 10K, 25K, 50K and 50 mile options on soft gravel loops with a single aid station per lap and inclusive entry policies.

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.

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.

A trail marathon and a 10 mile race at Teason's Woods in Palos Hills on May 9, 2026, using the Sag Valley Trail. Wide horse trails, multiple aid stations, pre assigned race day packet pickup, and a unique wooden finisher medal.

Trail Run Xtreme in Portage, IN on May 17, 2026 features a wooded single-track 12K and a 3K kids race with roots, mud, and possible water crossings. Post-race shirts, a meal, and age group awards are provided.

This 5-mile trail run honors Jennie Hamilton at Stoney Run County Park on Memorial Day. The course features natural trails with a possible pond crossing and offers a relaxed, inclusive atmosphere. Every runner gets a water bottle, with post..

Dirt Circus brings the trail running community together for a free festival in Crystal Lake. Enjoy a choice of group run distances, a vendor expo, food, and a raffle with prizes. Connect with local race directors and brands at this cupless,..

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..