Windsor
Trail Running Calendar near Windsor 2026-2027
Explore the top trail runs near Windsor for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Run or hike through Forest Ridge Preserve on October 3 to support Moreland Hills parks; proceeds fund trail and park improvements.
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.
February 2027
Trail races on 02/20/2027 at North Chagrin Reservation with 15K and 8K options plus a heated shelter and hot chocolate bar.
May 2027
A 24 hour trail endurance event on a 1 mile loop through woodland and rock formations near Kirtland, Ohio, with a 100 mile race option and timed entries.
Trail races at Shelterhouse Picnic Area on May 8, 2027 offering a 10k and a half marathon through forested single track and creek side paths.
September 2027
October 2027
Obstacle course races at Southington Off Road in Windham OH on Oct 30 to 31 featuring Sprint, Super, Beast, Ultra and kids races.