Naperville
Trail Running Calendar near Naperville 2026-2027
Explore the top trail runs near Naperville for 2026-2027! We've gathered 30 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Half marathon and 10K through Danada Forest Preserve on crushed limestone trails, USATF certified, chip timed with finisher medals and pacers for the half marathon.
A timed ultrarun in Chicago with 3 hour, 6 hour and 12 hour options on a roughly one mile loop, hourly playful challenges, on-course aid and relay team choices.
Turbo Trot in Geneva offers a 2.5 mile run, a 1 mile kids race and a mini road race rally for ages 3 to 8, with shirts, awards and a scholarship fundraiser.
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 up Mt. Hoy in Blackwell Forest Preserve, Warrenville IL, with proceeds funding two years of housing through Bridge Communities.
October 2026
A 2 to 3 mile run or walk on October 3, 2026 in Midlothian Meadows with a guided visit to Bachelors Grove cemetery and a post-event beer 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 in New Lenox on October 10 held on a cross country course with in person and virtual options to raise funds for men's mental health and suicide prevention.
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.
5K and 10K trail run and walk at Swallow Cliff South Forest Preserve in Palos Park, featuring gravel trails, sustainable race kits, and age group awards.
A nighttime trail event in Pingree Grove, Illinois featuring multiple 5K heats through haunted sets with animatronics and actors, plus a costume contest, bonfire, live entertainment and food.
Trail races at Deer Grove Forest Preserve on Oct 24, 2026 offering 50K, 25K and 5-mile options on a runnable 5.5 mile loop with stocked aid stations and cash prizes.
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 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.