There are 6 towns on the island of Martha’s Vineyard. The three down-island towns are Edgartown, Oak Bluffs and Vineyard Haven. Upisland, there is Aquinnah, Chilmark and West Tisbury.
Except for Oak Bluffs and Edgartown, the other towns on Martha’s Vineyard range from dry to moist. Chilmark is still very much that you can bring your own alcohol to a restaurant located in the town but they will not sell alcohol. Aquinnah and West Tisbury restaurants will sell beer and wine. You can bring your own liquor to add to mocktails provided.
Aquinnah is located at the very Western tip of Martha’s Vineyard. There’s the Aquinnah light house, the Wampanoag Cultural Center and a handful of shops. The houses are tucked away on large land lots here. Caroline Kennedy owns a large chunk of the area which she inherited from her mother.
Chilmark is sandwiched in between West Tisbury and Aquinnah. It’s perfect pastoral beauty – rolling hills and dry stone walls. Chilmark has a reputation for being the snootiest place on the island. Its got two very good town beaches, Squibnocket Beach and Lucy Vincent Beach.
West Tisbury is also more pastoral beauty. It’s reputation though is more hippy-dippy than snooty. There’s a charming little town with Alleys, an all-encompassing general store, a terrific library and art galleries. Every year the annual Livestock Show and Agricultural Fair is held in August in West Tisbury.
Edgartown is known for its elegant white Greek Revival houses built for the whaling captains when this town was the whaling capital of the area. Edgartown has lots of amenities such as hotels, restaurants, boutiques and museums.
Although an island, Chappaquidick is part of Edgartown. You get to Chappy by taking the dinky little car, bike and passenger ferry across Edgartown Harbour.
Chappy has got no amenities – just one store called appropriately The Only Store and looks something straight out of Deliverance. It’s home to the beautiful Cape Pogue Nature Reserve. One summer when some college kids threw a raucous party that lasted into the early hours of the morning at a house on Chappy, the neighbours complained. The Edgartown police had to walk up the ferry man and then take the ferry over to break up the party. Needless to say, they were not pleased.
Oak Bluffs started as a tent city which served as the camp ground for the annual Methodist camp meetings in the 19th century. Originally a part of Edgartown, Oak Bluffs became its own town. To the extent Martha’s Vineyard has a party town, Oak Bluffs would be it. There is live music, bars and dining options. Circuit Avenue is the main drag in town and filled with people late into the evening.
Vineyard Haven is the most practical of the towns on Martha’s Vineyard. It has year-round ferry service and so is the home of many year-round residents. There’s a charming Main Street with boutiques, restaurants and galleries.