Illinois
Illinois Trail Running Calendar 2026-2027
Explore the best trail runs in Illinois for 2026-2027! Our updated list features 91 exciting trail runs across the region. Find your next trail run in Illinois below and join the trail community at these great events!
September 2026
A dog friendly 2K and 5K fun run and walk at Case Creek Valley on September 20, 2026, with some proceeds supporting Rock Island County Animal Shelter.
QC JAVA JOG is a coffee themed trail race on September 20, 2026 at Case Creek Trails near Coal Valley IL with 2k and 5k courses through pastures and woodlands.
A 5K trail run or walk at Patriot's Park in Greenville on 09/26/2026 focused on community support for children and families affected by childhood cancer, with registration open 03/02/2026 and a $35 fee.
Experience a grassroots trail event in Dixon featuring loop-based distances from 8 miles to a 100 miler on a mix of singletrack and meadow paths.
Trail runs at Moraine Hills State Park on September 26 2026 with in person and virtual options across 5K 10K and half marathon distances.
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.
Test your endurance at this 6 or 12 hour timed race featuring a scenic 2-mile loop along the Evanston lakefront and Northwestern University campus.
A family-friendly color run in Freeburg, IL on September 26, 2026 that honors a life and raises awareness about distracted driving. The course includes color stations and an optional wooded trail with gentle hills and creek crossings.
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.
Nighttime community trail event at Lewis Park in Springfield on September 26, 2026, with torch lit 3 mile run and 1 mile walk; donations support trail upkeep.
October 2026
A point to point trail ultramarathon along the Hennepin Canal State Trail in Illinois, with 100 mile, 50 mile, 50K and a 100 mile relay.
Run The Woods is a trail event at Timber Pointe Outdoor Center in Hudson, IL featuring 5K and 8K races with youth divisions and a one mile untimed trail walk. Proceeds benefit Easterseals Central Illinois and Timber Pointe Outdoor Center.
Autumn Leaf Run is a 5K trail event at Oakdale Nature Preserve in Freeport on 10/03/2026. The looped course crosses prairies, creek and wooded trails and raises funds for park improvements through the Freeport Parks Foundation.
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 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.