Oak Forest
Trail Running Calendar near Oak Forest 2026-2027
Explore the top trail runs near Oak Forest for 2026-2027! We've gathered 23 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A memorial stair climb and one mile walk at Lake County Fairgrounds honoring 9/11 heroes, with wristbands naming a fallen first responder.
Timed 3, 6 and 12 hour ultra events at Horner Park in Chicago on a paved loop under one mile, featuring hourly challenges, one aid station, and relay options.
An obstacle course race at Indiana Dunes National Park on September 13, 2026, featuring 10k, 5K and a K9 3.1-mile event. The course uses varied landscapes to reflect terrains associated with military service.
Experience the Bloomingdale Trail Run in Chicago featuring a timed 5K and short dashes for youth. This annual event offers a variety of distances on an urban trail for a family friendly day of running.
A 30 minute run or walk on Mt Hoy in Blackwell Forest Preserve that raises funds to house a family for two years through Bridge Communities.
Community 5K run and 2K walk at Lake County Fair Grounds supporting oral cancer awareness; timed 5K, non-competitive walk, and event awards.
A family friendly 1 mile run or walk at Montessori School of Lemont with colorful water based sprays, a white event tshirt, and an eco friendly confetti pop.
October 2026
A 2 to 3 mile run or walk on October 3, 2026 in Midlothian Meadows with a guided visit to Bachelors Grove cemetery and a post-event beer and 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.
Don't Run Alone 5K in New Lenox on October 10 raises awareness for men's mental health with a 3.1 mile on-site course and a virtual 5K option.
5K and 10K trail run and walk at Swallow Cliff South Forest Preserve in Palos Park, featuring gravel trails, sustainable race kits, and age group awards.
Trail races in Willow Springs on a 5.5 mile loop offering 50K, 25K and a 5 Miler with stocked aid stations, prize money, and inclusive entry options.
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 with 8 mile two loop and 4 mile one loop options, post race chili and craft brews, plus age group and overall 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.
December 2026
A 4.5 mile trail race at Schiller Woods West with crushed limestone and single/double track, on-site packet pick-up, finish-line chili and post-race raffle.