Chilmark

Chilmark is up-island in every sense — winding rural roads, stone walls, and the working fishing harbor at Menemsha where the island still pulls in lobster and sword. Lucy Vincent is the cliff-backed sticker beach (resident-only in season), Menemsha’s public beach is the sunset-and-lobster-roll classic, and Squibnocket sits at the south-shore tip. There’s essentially no restaurant scene — drive to Edgartown or eat at Larsen’s on the dock.