Trail Running calendar near Yorkville 2026-2027

Experience ten miles of hills and winding trails through the Byron Forest Preserve and Nardi Equine Prairie. This cup free race features cash prizes and a post race celebration with pizza at Hairy Cow Brewing Company.

Event Details The Hindsight Ultra Trail Runs take place in Dixon, Illinois. The event offers four distances: a 100 Miler, a 100k, a 50k, and a 25K. The course consists of loops starting behind the Dixon Park District Facility. Each loop is..

The Bloomingdale Trail 5K is an annual family-friendly running event in Chicago. It features a timed 5K race alongside shorter dashes for young runners. Registration is available for all three distances.

A point to point, all trail ultramarathon along the Hennepin Canal State Trail in northwest Illinois. Multiple distances from 50K to 100 miles, with aid stations every 3 to 7 miles and a 30 hour cutoff for Western States qualification.

Run or walk through the scenic Timber Pointe Outdoor Center in Hudson. Choose from 8K and 5K races or an untimed 1 mile trail walk to support Easterseals Central Illinois.

Experience natural dirt trails and scenic views at this Janesville event featuring a competitive 5k run and casual walk. Stay for the heritage celebration with food trucks and live music after you finish.

Experience a chip timed 5k trail run through the diverse terrain and scenic landscapes of Oakdale Nature Preserve. All proceeds support local park projects and trail maintenance.

Join this community run and walk at Vollmer Road Grove Forest Preserve to support homeless school children. Participate in person on the paved 5K trail or join virtually to help provide essential school supplies for families in need.

Experience a fast and flat crushed gravel trail through the forests and wetlands of Lake County. Featuring four distances from a half marathon to a 50 mile ultra, these races offer a scenic out and back course perfect for personal bests.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

Take on the Soul Crusher trail run through the forested paths of Veteran Acres & Sternes Woods in Crystal Lake. The event features a 5-mile loop course with a chance for extra mileage, finishing with a unique skeleton medal. Prepare for a c..

Experience a haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

Fancy Nonsense 25k/50k The Fancy Nonsense 25k/50k is described as a nonsensical running experience born from mischief and imagination, designed to provide a space for the joy of running. The event takes place in the Palos Trail System at Re..

Celebrate Halloween and support animal shelters at this dog friendly 5k in Busse Woods. Enjoy a flat paved course with treats for both humans and leashed pets at the finish line.

A Halloween night run and walk through the Lake County Fairgrounds. The event includes a timed 5K and a non-timed 2K walk, costume prizes, and entry to a festive market. Bring a flashlight for the evening course.

Embrace an autumn adventure at the Big Timber XC Challenge, a trail run featuring a famous creek crossing through the woods of Camp Big Timber. Choose between a 3-mile or 5-mile course on grass and gravel paths. All runners get a shirt and..

Experience the Bigfoot Half Trail Run at Stoney Run County Park. This two loop course features a mix of grass, dirt trails, and gravel with manual timing and unique raffle prizes for participants.

Experience the diverse terrain of the historic Lemont Quarries with four trail race distances ranging from 10K to 60K. Runners navigate a mix of flat gravel paths and technical single-track trails through the woods.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

Celebrate Thanksgiving with a 2 mile run through the wooded trails of Sheffield Illinois. Wear your best holiday costume for a chance to win prizes at this untimed community event.