Naperville
Trail Running Calendar near Naperville 2026-2027
Explore the top trail runs near Naperville for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 5K and 10K trail run and walk through Swallow Cliff South featuring unpaved gravel trails, notable elevation, reusable race cups, and shirt style options.
A nighttime 5K trail run in Pingree Grove Illinois with ghostly actors and animatronics, plus a postrace DJ, contests, food, and a finisher medal and event t shirt.
A grassroots trail ultra at Deer Grove Forest Preserve on a 5.5 mile loop with 25K and 50K options, marked course, staffed aid stations, and prize money for top finishers.
November 2026
A 3 mile cross country event in Schaumburg on November 8, 2026 with separate men's and women's races and an optional team competition.
Trail races at Wolf Road Woods on November 21, 2026, offering 8-mile and 4-mile loop options with trail terrain, finisher chili, craft brews, and age-group 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.
Community cross-country event at Carraig Irish Pub offering a 5K run and a 1.5 mile walk, with apparel, a drink ticket, post-race food, and proceeds to local charities.
December 2026
December 12 2026 trail race in Schiller Woods Chicago, a 4.5 mile off-road course with on-site water, post-race chili and brews, plus age group and overall awards.
January 2027
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.
February 2027
Trail races at Oakhurst Forest Preserve in Aurora, Illinois, the series includes 5K, 8K, and 10K events in early 2027 with a single registration and series swag rewards; the 8K fee is $65.00.
March 2027
A 10K trail race at Hickory Knolls Discovery Center in St. Charles, IL with a $70 entry fee. The race is part of a winter series that also includes a 5K and 8K and uses a single registration page.
April 2027
May 2027
Flat out and back half marathon and 10K on the limestone Great Western Trail with a 25 plus year history and proceeds supporting local mental health charities.
Trail marathon and 10 mile on Sag Valley Trail through Cap Sauers Nature Preserve with wide horse trail, multiple aid stations, and notable elevation.