Windsor
Trail Running Calendar near Windsor 2026-2027
Explore the top trail runs near Windsor for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A 5K cross country race at Penitentiary Glen Reservation in Willoughby on August 18, 2026. The course mixes grass fields and crushed limestone trails, with separate races for male and female competitors and open entry for kids and adults.
October 2026
A community event at Forest Ridge Preserve featuring a chip timed 5K and a 1.5 mile self guided hike through the Chagrin River valley. Proceeds support the Moreland Hills Parks Commission and registrants by September 20 receive a commemorative shirt.
A 5K trail run at Brant's Apple Orchard in Ashtabula on October 3 with vineyard and woods terrain, creek crossings, and cider plus an apple donut at the finish.
Outlast Cleveland is a 6 hour trail endurance challenge in Garrettsville, OH where runners complete a 5K every hour for six rounds. Finish all six to earn the OUTLAST medal and a place on the national leaderboard.
November 2026
Fall trail race at North Chagrin Reservation on Nov 7, 2026 with looped distances from 5K to 100K, ruck divisions, chip timing, and an optional hill climb at Squire's Castle.
A two-loop trail running event at North Chagrin Reservation in Willoughby Hills, Ohio, the Dirty Dirty 15K is the final race of the Dirty Trail Series, passing Squires Castle, Buttermilk Falls and Oxbow Lagoon and ending with a series party.
October 2027
Two-day Spartan Trifecta Weekend near Cleveland with Sprint 5 km, Super 10 km, Beast 21 km and Ultra 50 km across rugged forest trails.