Trail Running calendar near Chicago 2026-2027

Trail run at Saw Wee Kee Park on October 17, 2026, over soft, twisting trails with variable footing. Bib-timed waves, part of a four-race series with collectible medal pieces and seasonal swag.

A timed trail event at St. Patrick's County Park in South Bend on October 17, 2026, offering 24 Hour, 12 Hour, and 6 Hour races. The loop is mostly dirt and grass with short asphalt crossings and proceeds support the ALS community.

Trail race in Crystal Lake through Veteran Acres and Sternes Woods with 5 and 10 mile options, packet pickup on Friday and race morning, cup-less course, and finishers' medals and shirts provided.

A fall event at Richardson Adventure Farm in Spring Grove on October 18, 2026 featuring a 10K, two 5K options including a corn maze route, a 1-mile family adventure, chip timing, and a finisher medal for every participant.

A Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.

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.

Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.

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.

Trail running at Camp Big Timber in Elgin, IL on November 8, 2026, featuring 3 and 5 mile perimeter courses with a creek crossing. A kids fun run and a pancake breakfast are included, and proceeds support local youth organizations.

Bigfoot Half Trail Run at Stoney Run County Park in Hebron IN is a two-loop trail race over mixed surfaces with aid stations, packet pickup, raffle items for park fundraising and manual finishing with numbered popsicle sticks.

A trail festival in Lemont on November 14, 2026, offering 10K, 20K, 30K and 60K on single and double-track trails and gravel around the Lemont Quarries and I&M Canal, with multi-lap courses and variable terrain.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

The St. Joe Valley Happy Trail Run will take place in Roseland from Saturday 14 November 2026 to Monday 16 November 2026. You can run between 5 and 13 miles.

A trail based Turkey Trot at Southwestern Michigan College offering 10K, 5K and a free 1K kids run, chip timed with live results, guaranteed tech shirts for early registrants and age division medals.

A Thanksgiving 5K on the Green Bay Trail at Winnetka Train Station featuring rolling start waves, a family division, packet pickup before race day, post-race refreshments, and support for local charities.

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.

Regional cross country championships in Kenosha, WI on November 28, 2026, featuring multiple 5K races and a 3K youth event. Top finishers in the championship race can qualify for the Brooks XC National Championships in San Diego.

A public cross country race in Evanston with three all-grass loops, team and individual scoring, included long-sleeve race shirt, and a post-race awards cookout; entry fees vary by registration date.

A dog-focused trail run at Lake Geneva Ziplines and Adventures offering one or two loops on winding singletrack. Canicross and dog friendly options are available, with podium awards reserved for dog-equipped finishers and a finisher gift fo..

A winter trail series at Dick Young Forest Preserve in Batavia featuring 5K, 8K, and 10K races on separate dates in early 2027, with combined registration and a series swag reward program.