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
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 races at Camp Big Timber on November 8, 2026 featuring roughly 3 and 5 mile perimeter loops, a kids fun run, creek crossings, postrace pancakes and awards.
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.
Experience the diverse terrain of the historic Lemont Quarries with four trail race distances ranging from 10K to 60K. Runners navigate a mix of flat gravel paths and technical single-track trails through the woods.
A certified multi-distance ultramarathon in Vienna, IL on the Tunnel Hill State Trail featuring 100 mile, 100 km, 50 mile USATF nationals and a marathon with certified courses.
Experience the trails of Mcnaughton Park in reverse at this Illinois event featuring distances from 3.5 miles to a 50 miler with creek crossings and significant elevation.
Run or walk a scenic 5K trail in Palatine with your dog to support student scholarships and pancreatic cancer awareness at this family friendly community event.
Trail race at Harms Woods North in Morton Grove with 3, 6 and 9 mile loop options and aid at the start of each lap.
Community 5K and kids fun runs at Farmingdale Elementary on November 14, 2026, raising funds for the school.
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.
Celebrate Thanksgiving with a 2 mile run through the wooded trails of Sheffield Illinois. Wear your best holiday costume for a chance to win prizes at this untimed community event.
A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.
Thanksgiving morning 5K on the Green Bay Trail in Winnetka with rolling starts, three waves including a family division, packet pickup and postrace refreshments.
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.
A community Turkey Trot at NorthPointe Health & Wellness on November 26 2026 featuring a chip timed 5K and a non timed 0.5 mile Tiny Trot for all ages.