Illinois
Illinois Trail Running Calendar 2026-2027
Explore the best trail runs in Illinois for 2026-2027! Our updated list features 95 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
A 5K run and walk at College of Lake County Grayslake on October 4, 2026 raising funds for the Carrera de los Lancers Scholarship and student entrepreneurship programs.
Test your limits at Arrowhead Lake Campground on a flat 2.07 mile lakeside loop with timed options ranging from 3 to 24 hours.
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.
Trail races in Lake County, Illinois offering 50 Mile, 50K, Marathon and Half Marathon on a flat crushed gravel course with timed cutoffs and multiple aid stations.
Experience the diverse terrain of Farmdale Reservoir in Illinois with trail races ranging from a 10K to a 100 mile endurance run.
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.
Shake Your Trail Feather Trail Run at Willenborg Woods on October 18 offers distances from a 5K to a 100K across timber, riverside paths, creeks and hills. The event features full course marking, community support and a post-race celebration.
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.
Experience a single track trail adventure through Veteran Acres and Sternes Woods in Crystal Lake featuring 5 and 10 mile distances and custom skeleton medals.
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 fall event at Richardson Adventure Farm in Spring Grove, IL with a 10K, a 5K through a corn maze, and a 1 mile family adventure, plus finisher medals for all.
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 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.
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.
Experience the wooded trails of Coal Hollow Park with a scenic 5K walk or trail run followed by community celebrations at local venues.
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.
A fall event at Allerton Park featuring a 5.7 mile trail run, a 2 mile nature walk, and a virtual 5.7 mile option. The riverside course has roots, ruts, and sharp turns, with awards, costume prizes, and park donations.
First edition trail 5K run and walk at Rainbow Scout Reservation in Morris, IL on October 25, 2026, with registration Aug 25 to Oct 5 and a $30 fee.