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Trail Running Calendar Illinois 2025-2026

We have found 48 Trailruns in Illinois. Check below where and when you can find the races.

Haunted Highlander Assault Trail Run

McHenry

Join the Haunted Highlander Assault Trail Run in McHenry on October 3, 2026 for spooky 5 km heats through haunted sets and animatronics. After the run enjoy a costume contest, bonfire, live entertainment and food.

Shake Your Trail Feather Trail Run

Charleston

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Shake Your Trail Feather runs October 16 and 17, 2026 at Willenborg Woods in Charleston, IL, with distances from 100K to 5K on winding single track, creek crossings and riverside paths. Friendly trail support and a post race celebration awa..

Jaimie Cox Memorial Run

Roscoe

Join the Jaimie Cox Memorial Run in Roscoe IL on October 17, 2026 for a family friendly 5K or 2 mile walk along the scenic Stone Bridge Trail. Run for a cause as proceeds support the Jaimie Cox Memorial Scholarship.

Allerton Park Trail Run

Monticello

Run or walk through Robert Allerton Park on October 25, 2026 with a scenic and challenging 5.7 mile trail run, a relaxed 2 mile nature walk, or a virtual option. A portion of proceeds helps maintain trails and park amenities.