Gary
Trail Running Calendar near Gary 2026-2027
Explore the top trail runs near Gary for 2026-2027! We've gathered 18 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
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.
A 10 hour trail endurance event at Bluhm County Park on August 29, 2026 with hourly loop cutoffs, chip based prizes, and a race t shirt and wooden medal.
September 2026
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.
October 2026
Trail runs and a fun run/walk on a 4-mile loop at Tryon Farm, with multiple distance options and aid at the main station.
Trail races at Creekside Trails in Valparaiso on October 3, 2026: a 5K loop and a 30K team relay hosted by local firefighters.
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 half trail run at Stoney Run County Park in Hebron, IN on November 14, 2026, over grass, pavement, gravel and single-track trails with aid stations and packet pick-up.
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
30k, 50k and 50 mile trail races at Sunset Hill Farm County Park in Valparaiso, IN with one aid station, a 16 hour finish window, and distance-specific finisher awards.
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.