Oak Forest
Trail Running Calendar near Oak Forest 2026-2027
Explore the top trail runs near Oak Forest for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Looped trail races at Deer Grove Forest Preserve in October 2026 offering 5 mile, 25K and 50K distances with aid stations, prize money, and a grassroots community atmosphere.
Nighttime 5K and 2K run and walk at Lake County Fairgrounds in Crown Point with costume prizes, awards, finisher medals for the first 300, and market entry.
November 2026
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.
Community cross-country event at Carraig Irish Pub offering a 5K run and a 1.5 mile walk, with apparel, a drink ticket, post-race food, and proceeds to local charities.
December 2026
December 12 2026 trail race in Schiller Woods Chicago, a 4.5 mile off-road course with on-site water, post-race chili and brews, plus age group and overall awards.
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.
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.
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.