Activities
Thank You for Another Successful Trail Run!
On Saturday, September 7th, Sheriff’s Meadow Foundation hosted the Second Annual Trail Run at Caroline Tuthill Preserve in Edgartown. The Preserve boasts over 150-acres of oak and pitch pine forest, open meadow, and salt marsh along Sengekontacket Pond, with the Trail Run traversing a 3.2 mile loop throughout. This year, 44 participants crossed the finish line!
We would like to extend our heartfelt gratitude to our sponsors, Cronig’s Markets and Island Source, for their continued support of this event; and to Reann Steenkamp and Dianne Booth of MV Running Company for providing their incredible knowledge and timing services. We also recognize Jon Malone of Edgartown Bikes for leading the way for the runners, from start to finish, on his mountain bike.
Bravo to all who participated! Special congratulations to Chris Cajolet of Edgartown, who crossed the finish line first, and to Bryn Willingham, who was the womens’ overall champion for the second year in a row!
Thank you again for an incredible event – we look forward to sharing details of our Third Annual Trail Run in 2025!

Parking is located at the Edgartown Park-and-Ride which is located by the Edgartown triangle and is free of charge. Please cross Edgartown-Vineyard Haven Road at the designated crosswalk and continue along the north side of the road to access the start line. Participants are encouraged to carpool or take public transportation if possible. Bus route schedules can be found here. If you are arriving from off-island please review the ferry schedules here. We are unable to provide transportation from the ferry terminals.