Oak Forest
Trail Running Calendar near Oak Forest 2026-2027
Explore the top trail runs near Oak Forest for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Half marathon and 10K through Danada Forest Preserve on crushed limestone trails, USATF certified, chip timed with finisher medals and pacers for the half marathon.
Memorial stair climb and one mile walk in Crown Point on September 11, 2026, featuring 1,980 steps to honor 9/11 heroes.
A timed ultrarun in Chicago with 3 hour, 6 hour and 12 hour options on a roughly one mile loop, hourly playful challenges, on-course aid and relay team choices.
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 up Mt. Hoy in Blackwell Forest Preserve, Warrenville IL, with proceeds funding two years of housing through Bridge Communities.
October 2026
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 small autumn run from Rubio Woods to Bachelors Grove Cemetery with a guided legend tour, long sleeve shirt, raffle and a post run beer; entry fees vary.
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.
Trail 5K and 10K runs and walks through Swallow Cliff Woods in Palos Park with gravel trails, notable elevation, reusable race cups and shirt options.
Trail races at Deer Grove Forest Preserve on Oct 24, 2026 offering 50K, 25K and 5-mile options on a runnable 5.5 mile loop with stocked aid stations and cash prizes.
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
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.
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.