Windsor
Trail Running Calendar near Windsor 2026-2027
Explore the top trail runs near Windsor for 2026-2027! We've gathered 10 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A 5K and an 800 m kids run through the Orange City Schools campus on September 27, 2026, with proceeds benefiting the OHS Cross Country team.
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.
12th annual 5K run/walk through vineyard, woods, and orchard trees in Ashtabula with varied terrain, creek crossings, and cider and donuts at the finish.
Two hour night event at Geauga Park District where participants run, jog, or walk as many 0.85 mile laps as possible to earn a Space Race medal and planet ribbon.
A course preview for Conquer the Castle at AB Williams Memorial Woods in Mayfield on October 10, 2026, featuring an unmarked loop of about 10 miles with no aid stations.
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.
September 2027
October 2027
Two day Spartan Trifecta Weekend at Southington Off Road in Windham OH with Sprint, Super, Beast, Ultra and kids obstacle races plus a Trifecta pass.