Illinois
Illinois Trail Running Calendar 2026-2027
Explore the best trail runs in Illinois for 2026-2027! Our updated list features 77 exciting trail runs across the region. Find your next trail run in Illinois below and join the trail community at these great events!
October 2026
Multi-distance trail races through single track timber, riverside paths and creeks at Willenborg Woods in Charleston, IL on October 16 and 17, 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.
Nature-based out-and-back event in Roscoe, IL offering a 5K run or 2 mile walk on mixed gravel and crushed limestone, starting at Roscoe Middle School and passing a water station twice.
Trail race in Crystal Lake, Illinois on October 17, 2026 featuring single track forest loops with 5 and 10 mile options and race shirts plus finisher medals.
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.
Runs at Richardson Adventure Farm in Spring Grove include a 10K, a corn maze 5K with over 250 turns, a farm 5K, and a kids 1 mile.
A chip timed 5K and an untimed 1 mile fun walk at GE Park in Bloomington on October 18, 2026, raising funds for BN Sunrise Rotary Youth Services and the CCHS Rotaract Club. Awards include ceramic steins for top 5K age group finishers.
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.
Looped trail races at Deer Grove Forest Preserve in October 2026 offering 5 mile, 25K and 50K distances with aid stations, prize money, and a grassroots community atmosphere.
Originally listed as a 5K at Washington Park in Springfield with registration closed and a $30 fee; a notice states the event has been renamed and moved to September 5th.
Hills & Hollow 5K at Coal Hollow Park on October 24, 2026 offers a trail run and a 5K walk; $35 entry with proceeds supporting the Chillicothe Parks Foundation.
5.7 mile trail run, 2 mile nature walk, and a virtual 5.7 mile option at Robert Allerton Park on October 25, 2026, with varied terrain and park support.
A 5K trail run and walk at Rainbow Scout Reservation in Morris, IL, with a $30 fee that includes a Sport-Tek shirt and patch; proceeds support the Scouting program.
Family-friendly 5K and 1-mile walk/run at Lakeland Park on October 31, 2026, hosted by the Canton YWCA with proceeds supporting local YWCA programs.
A Halloween-themed trail event at Friends Creek Conservation Area featuring a costumed 5K and a kids 880 yard dash with costume prizes and goody bags.
Trail races and a one mile fun run around Beaver Dam State Park raising funds for the Macoupin Center for the Developmentally Disabled.
November 2026
Annual 5K and 10K runs plus a 5K walk and virtual options around Meadowbrook Park in Urbana to benefit Grand Prairie Friends.
Nighttime trail running at Illiniwek Forest Preserve with 7K and 14K courses, required headlamps, aid stations, and postrace fire and live music.
Trail race at Camp Big Timber on November 8, 2026 with 3 and 5 mile courses, a cold creek crossing, a kids run and a pancake breakfast supporting local Scouts and Elgin Sharks.