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Illinois Trail Running Calendar 2026-2027

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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!

May 2027
An obstacle course event at Byron Motosports Park on May 22, 2027 offering 10K and 5K waves, Special Forces, Ruck division and a kids course, produced by a nonprofit honoring service members.
An 8K trail race and pond side kids fun run at Lincoln Memorial Garden in Springfield on May 22, 2027, featuring varied trail surfaces, participant shirts, and age group awards.
June 2027
Test your endurance at Willenborg Woods in this Bronze Ticket Backyard Ultra featuring a scenic 4.167 mile loop through trails and country roads.
Trail races at Waubonsee Community College on June 12, 2027 featuring chip timed 5K and 10K options, packet pickup choices, live results, and awards for the fastest female and male finishers.
Vineyard 5k at Mackinaw Valley Vineyard and Winery on June 13, 2027 with post race wine, chip timed results, and age group awards.
July 2027
A multi-distance weekend trail event at Camp Wokanda near Chillicothe IL with looped courses on the Illinois River Bluff Trail, including a 100 mile option with significant elevation.
A 3rd annual cross country 5K in Carterville with team and individual competition, grass and gravel course, standard XC scoring, and awards for top finishers and teams.
August 2027
A Scottish Highlander themed obstacle race in Pingree Grove on August 7, 2027 offering 50K, 15K, 5K, family 3K, a torch lit night run and a haunted 5K.
Night trail races in Dixon, IL on a ~5-mile loop with 5, 10, 15 mile options and a 3-person relay, one aid station, participant tee, and awards.
A multi-distance trail race weekend at Camp Ondessonk in Ozark, IL featuring technical singletrack, multiple waterfalls, five aid stations, and finisher awards for each distance.
Test your teamwork at Richardson Adventure Farm with 5 km, 15 km, or multi-lap Infinity courses featuring iconic obstacles and varied terrain.
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