Herriman’s great-grandfather was a white New York sea captain and slave owner who fathered children in New Orleans with a “free woman of color.”

Down island is more densely populated, and Edgartown, particularly, retains the flavor of the whaling industry, with its sea captains’ homes and bustling mercantile feel.

And yet he ended life in scandal, living with a secret mistress under the assumed identity of a sea captain.