Illinois
Illinois Trail Running Calendar 2026-2027
Explore the best trail runs in Illinois for 2026-2027! Our updated list features 82 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.
A 5K run/walk at Deer Park Golf Club in Oglesby, Illinois on November 7, 2026, on a mostly flat golf course with post-race drinks, shirts while supplies last, and age-group awards.
Trail runs at Camp Big Timber on November 8, 2026 with 3 and 5 mile loops, a kids run, creek crossing, participant shirts and pancake breakfast.
A 3 mile cross country event in Schaumburg on November 8, 2026 with separate men's and women's races and an optional team competition.
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 flat, crushed limestone out and back in Vienna Illinois offering 100 mile, 100 km, 50 mile and marathon distances and hosting the 2026 USATF 50 Mile Championships.
Trail races at McNaughton Park in Pekin, IL offering 3.5, 10, 30 and 50 mile courses on a 10 mile loop run in reverse direction.
A scenic 5K in Deer Grove on November 14, 2026 that welcomes runners, walkers and canicross teams while raising funds for a local scholarship.
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 with 8 mile and 4 mile options, shirts, finish-line chili and brews, plus awards and a post-race raffle.
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.
54th Annual Rockford Road Runners Turkey Trot is an approximate 5K trail race at Atwood Park with chip timing, day of packet pickup, and donations for local charities.
A chip timed 2.5 mile cross country Turkey Trot in Orland Park on Thanksgiving morning, with race shirts, a 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.