Orland Park
Trail Running Calendar near Orland Park 2026-2027
Explore the top trail runs near Orland Park for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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 guided two to three mile run and cemetery tour in Midlothian with a post event beer, shirt 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.
A fall trail run and walk in Swallow Cliff South offering 5K and 10K routes on mostly gravel, hilly trails with sustainability features and guaranteed race items for early registrants.
Chicagoland trail ultra at Deer Grove with repeated 5.5 mile loops, stocked aid stations, community focus, 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
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.
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.