Trail Running calendar near Chicago 2026-2027

This community 5K run/walk supports homeless school children in the Chicago suburbs. Participants follow a paved trail at the Vollmer Road Grove Forest Preserve. The event includes a virtual option and aims to raise funds for essential scho..

This 7km trail run at Potato Creek State Park features wide, stable paths and two notable hills, making for a fast yet challenging loop. It's a bonus point event for the DINO Trail Run Series. Top finishers and age group winners earn medals..

The Trail Golf Endurance Challenge reinvents trail running with a golf-inspired scoring system. Runners tackle 3-4 mile "Holes" on the hour, aiming for the lowest stroke score over a 50K or 10-mile course. It's a unique test of pacing and s..

Celebrating its 45th year, the YMCA Brickyard Run features a 5 Mile Gold Cup race, a 5K for younger runners, and a new 2K Family Fun Run/Walk. The event is known for its unique brick awards and supports a local YMCA scholarship fund.

A cross-country event in Williams Bay featuring a 5K run/walk and a children's quarter mile walk/run. The course follows grass trails through hills, woods and prairie, with parking and restrooms provided.

A summer trail running event on the scenic Creekside Trails in Indiana. Choose from 4, 9, or 18-mile distances on a course with single-track, bridges, and rolling terrain. The race features inclusive policies and support for youth and under..

Run a chip-timed 5K or join a scavenger hunt 3K walk at St. Patrick's County Park. Everyone gets a handcrafted medallion, plus there's an egg bake breakfast and door prizes. Leashed dogs are welcome on the walk.

Run the Rails offers a unique 1, 4, or 7-mile run starting from Prairie Park in Elburn. The courses cross a rail line bridge, providing views of the surrounding countryside. This community event supports the Elburn Parks Commission.

The Summer Trail Classic offers three distances on the single-track trails of Paul Douglas Forest Preserve. It's the third race in a yearly trail series, with proceeds supporting local trail maintenance. Participants receive a running vest..

The Naperville Trails Half Marathon & 10K is set for September 5, 2026 in Wheaton, Illinois. Runners can choose from half marathon and 10K distances, with virtual options also available.

The Bloomingdale Trail 5K will take place in Chicago on Saturday 26 September 2026. You can run 5 kilometers.

Explore a multi-loop trail course at Tryon Farm in Michigan City. The 50k runs on a 4-mile loop featuring fields, dirt trails, and minimal pavement. Proceeds support the Tryon Farm Institute.

The Des Plaines River Trail Races will take place in Lake County on Saturday 10 October 2026. You can run between 21 and 80 kilometers.

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..

A 5k trail event in Pingree Grove that combines haunted sets, animatronics, and actors with multiple 5k heats; the day also features a costume contest, bonfire, live entertainment and food options.

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..

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..

The Bigfoot Half Trail Run takes place on a mixed-terrain course in Stoney Run County Park. This event features an on-course raffle, old-school timing with popsicle sticks, and a unique Bigfoot hat for participants. Aid stations are availab..

A trail race at The Forge in Lemont, IL on November 14, 2026 offering 10K, 20K, 30K and 60K on single and double track trails with variable surfaces, an aid station for multi-lap races, and a 400-runner cap.