Orland Park
Trail Running Calendar near Orland Park 2026-2027
Explore the top trail runs near Orland Park for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Loop based endurance event at Busse Woods on August 15, 2026 offering repeated 3.1 mile laps over smooth crushed limestone and packed gravel. Distances range from 5K to 50K with a central aid station and open loop format.
Continuous 3.1 mile loop at Busse Woods near Elk Grove, IL offering 40 and 50 mile options with a fully stocked aid station every lap and a 12 hour cutoff. Runs alongside The Next Loop series but is scored separately.
Alumni cross country meet in Chicago Heights on August 15 2026 using the old 2 Miles course with decade-based teams, chip timing and place-based scoring.
September 2026
USATF certified half marathon and 10K on crushed limestone trails at Danada Forest Preserve with chip timing, pacers, shuttle parking and finisher medals.
A remembrance event at the Lake County Fairgrounds Grandstand in Crown Pont, IN where participants climb 17 laps totaling 1,980 steps or join a 1 mile non timed walk. The event includes hero wristbands, limited finisher medals, and supports SWAT T to..
A timed urban ultra at Horner Park offering 3, 6, and 12 hour options on a short paved loop. Hourly playful challenges, a single aid station, and two- or four-person relay options add variety.
A one day trail running festival in Beecher, IL offering natural-terrain distances from 3 to 31 miles, cupless aid stations, finisher shirts and medals, a ruck category with weight rules, and awards including a DFL prize for the 50K.
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 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 trail ultramarathon at Red Gate Woods near Chicago offering 25K and 50K on a clockwise single track loop of about 5.5 miles, with staffed aid stations, course maps, and no pacers allowed.
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 the Sag Valley Trail at Cap Sauers Nature Preserve in Palos Hills, IL, with wide horsetrail, notable elevation gain, and staffed aid stations along the routes.
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.