Naperville
Trail Running Calendar near Naperville 2026-2027
Explore the top trail runs near Naperville for 2026-2027! We've gathered 29 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.
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.
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.
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 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.
A 5K trail event in Pingree Grove featuring haunted sets, animatronics, multiple heats, a costume contest, bonfire, live entertainment, food, and free parking.
Chicagoland trail ultra at Deer Grove with repeated 5.5 mile loops, stocked aid stations, community focus, and cash prizes.
Community 5K and 1 mile kids color run in Fox Mill, Saint Charles IL on October 24, 2026, with free registration and timed results by email.
November 2026
A 3-mile cross-country race at the MacNider course in Schaumburg on November 8, 2026, with separate women's and men's races, optional team scoring, pre-race packet pickup, and a $25 registration fee.
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.
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.