Chicago
Trail Running Calendar near Chicago 2026-2027
Explore the top trail runs near Chicago for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A 3 mile cross country event in Schaumburg on November 8, 2026 with separate men's and women's races and an optional team competition.
Trail races at Wolf Road Woods on November 21, 2026 with 8 mile and 4 mile options, shirts, finish-line chili and brews, plus awards and a post-race raffle.
A chip timed 2.5 mile cross country Turkey Trot in Orland Park on Thanksgiving morning, with race shirts, a raffle, and prize turkeys for top finishers.
A cross country event at Gaelic Park in Oak Forest on November 29, 2026 offering a 5K run and a 1.5 mile walk with proceeds to Gaelic Park Charities.
December 2026
A 4.5 miles trail race at Schiller Woods West Forest Preserve on December 12, 2026 featuring crushed limestone single and double track, post race chili and brews.
March 2027
Mudhen 5k Trail Run at Big Marsh Park in Chicago on March 13, 2027, is a 5K trail run with a course map; registration is listed as $0.00.
April 2027
May 2027
Trail marathon and 10 mile on Sag Valley Trail through Cap Sauers Nature Preserve with wide horse trail, multiple aid stations, and notable elevation.
Looped trail endurance event in Wolf Road Woods offering 7 or 11 hours on a four mile singletrack with an aid station stocked with hot dogs and pixie sticks.
Chip-timed 10K at The Forge Lemont Quarries on May 16, 2027, on mostly crushed limestone trails with quarry views and overall plus age-group awards.
September 2027
Both in person and virtual races in Wheaton, IL on September 11, 2027 offer half marathon and 10K distances with separate registration windows.
Obstacle course races at Indiana Dunes National Park on September 12, 2027 include 6.2 mi, 3.1 mi and a K9 3.1 mi course inspired by military landscapes.
A family-friendly 5K at Danada Forest Preserve supporting Inside Out Club, open to kids ages 4+, with a kids fun run, team and individual awards.