Six Towns, One Island
Each town has its own day
The Vineyard is six towns, three down-island and three up-island, each with a different personality. You can do a long weekend by basing in one and visiting the others, or split a week across two.
Town
Oak Bluffs
Pastel gingerbread cottages, the Flying Horses Carousel, Inkwell Beach, and the busiest summer ferry dock. Best in the morning before Circuit Avenue fills up.
Town
Edgartown
White picket fences, sea captains’ houses, the lighthouse, and a two-minute ferry to Chappaquiddick. The polished town.
Town
Vineyard Haven (Tisbury)
The working ferry harbor, year-round Main Street with bookshops and bakeries, and a quieter morning coffee than Edgartown or Oak Bluffs.
Town
Aquinnah
The island’s westernmost town, Wampanoag tribal land, and home to the red clay cliffs and Gay Head Light.
Town
Chilmark & Menemsha
Stone walls, quiet roads, and a small working fishing harbor with the island’s most loved sunset.
Town
West Tisbury
Farm stands, Polly Hill Arboretum, the Saturday farmers’ market, and a real sense of the island’s rural heart.