Trail Running Calendar Illinois 2026-2027

Trail runners in Decatur can choose between 4.4 and 7.6 mile courses on the fast rolling terrain of the Sand Creek Conservation District. Registration includes a tech shirt and finisher medal, with race proceeds supporting the Special Opera..

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.

This trail run/walk in Greenville's Patriot's Park is a 5K event supporting childhood cancer research. It takes place on scenic trails and is inspired by a personal story of courage.

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 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.

This trail running event at Willenborg Woods offers distances from a 5K to a 100K on scenic, handcrafted trails through timber and along creeks. It focuses on a community atmosphere with full course support and a post-race celebration. Pets..

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..

The Washington Park Trail Trek is a 5K run and walk on the forest trails of Springfield's Washington Park. The event supports the restoration of the historic Leland Farm Summer Kitchen. It is the final race in a series where participants ca..

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.

Experience a 5.7 mile trail race or a 2 mile nature walk along the Sangamon River at Robert Allerton Park. This community event supports local trail maintenance and features a costume contest in a scenic meadow setting.

Experience the beauty of the Illinois tallgrass prairie at Meadowbrook Park with 5K and 10K events supporting local land conservation. Runners and walkers of all ages are welcome to this annual community tradition.

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..