Trail Running calendar near Windsor 2026-2027

A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.

A chip timed 5K at Ledge Rock Hill Winery in Lake George on May 16, 2027, run and finish on a mostly grass cross country course with mildly challenging terrain. Registration includes a T shirt, collapsible wine glass, finisher medal, and a..

A mountain trail event at Plattekill in Roxbury NY on June 6, 2027, featuring a 6.5 mile course with 3500 ft ascent and a steep 5k. Awards and finisher swag are planned for top finishers.