Sheriff's Meadow Foundation Trail Run

Sheriff's Meadow Foundation Trail Run takes place in Edgartown, Massachusetts, on October 24, 2026 at 10:00 a.m. The annual event is held at the Caroline Tuthill Preserve over a 5K loop, 3.1 miles, on varied ground that includes woodland and salt marsh, sand and dirt trails, and a raised boardwalk section. Bibs can be collected the day before or on race morning at the start and finish area.

A trail 5K reads differently from a road one. Sand and boardwalk both change your footing and your rhythm, so run this by feel and accept that your split will be slower than a road 3.1 miles without meaning anything about your fitness. Trail shoes with real grip are worth having. Preparation is modest — a few weeks of running off pavement, including one longer trail run each week, is plenty for the distance.