The largest offshore island in New England, twenty-mile-long MARTHA’S VINEYARD encompasses more physical variety than Nantucket, with hills and pastures providing scenic counterpoints to the beaches and wild, windswept moors on the separate island of Chappaquiddick.
Martha’s Vineyard’s most genteel town is Edgartown, all prim and proper with its freshly painted, white clapboard colonial homes, museums and manicured gardens. The other main settlement, Vineyard Haven, is more commercial and one of the island’s ferry ports. Oak Bluffs, in between the two (and the other docking point for ferries), has an array of fanciful wooden gingerbread cottages and inviting restaurants. Be aware of island terminology: heading “Up-Island” takes you southwest to the cliffs at Aquinnah (formerly known as Gay Head); conversely, “Down-Island” refers to the triumvirate of easterly towns mentioned here.