Oak Forest
Trail Running Calendar near Oak Forest 2026-2027
Explore the top trail runs near Oak Forest for 2026-2027! We've gathered 17 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 2 to 3 mile run or walk in Rubio Woods with a guided visit to Bachelors Grove cemetery, a long sleeve shirt, post-event beer and a raffle.
The Lockport Fire Foundation presents the second annual Fire Zone 5k, a community 5k run and walk on a marked loop of the Forest Preserve trail starting at Hassert Park. Registered participants present on race day receive a t shirt and finisher medal..
A community 5K in Flossmoor with a parallel virtual 5K that raises funds and collects goods to support local families experiencing hidden homelessness and provide school supplies for homeless children.
A 5K timed race and an untimed 2K through the hilly 144-acre Camp Triangle Hills at Crossroads YMCA, held as part of Fall Fest with family activities like rock climbing, archery, tractor rides and a petting zoo.
A 5K walk and run on October 10 supporting men's mental health with an in person course in New Lenox and a virtual 5K option.
A 5K and 10K trail run and walk through Swallow Cliff South in Palos Park on October 17, 2026, with gravel trails, elevation changes, reusable race cups, and age group awards.
A grassroots trail ultra at Deer Grove Forest Preserve on a 5.5 mile loop with 25K and 50K options, marked course, staffed aid stations, and prize money for top finishers.
A Halloween themed nighttime run and walk at Lake County Fairgrounds in Crown Point on October 30, 2026. The event features a 5K and a non timed shorter course, costume prizes, awards, and entry to the Hometown Hocus Pocus Market.
November 2026
Trail races at Wolf Road Woods on November 21, 2026, offering 8-mile and 4-mile loop options with trail terrain, finisher chili, craft brews, and age-group awards.
A 2.5 mile chip timed cross country Turkey Trot on Thanksgiving morning in Orland Park, with long sleeve race shirts, a post race raffle, and prize turkeys for top finishers.
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
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
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
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.