Let’s see if we can make this confusing: Tisbury is the official name of Vineyard Haven, and Vineyard Haven is the main year-round town on the Island, but Vineyard Haven was not originally the town center of Tisbury, which was actually what is now called West Tisbury. And it wasn’t called Tisbury or West Tisbury, but Middletown, while Vineyard Haven was really called Holmes Hole, which was a corruption of Homes’ Hole…and on and on, back to the Wampanoag name Nobnocket and beyond.
All that being said, there’s little doubt that the sheltered waters of Vineyard Haven Harbor were visited by sailing vessels for decades before the 1660s and 70s, when various English families began to build houses around the harbor and the lagoon. By the end of the 1700s, the route up and down the coast through Vineyard and Nantucket Sounds made those bodies of water second only to the English Channel in terms of shipping traffic, and Vineyard Haven had grown into a bustling port town with about 350 residents. There were salt-works, ship’s chandleries, ropewalks, sail lofts, blacksmith shops, a harness factory, and an assortment of inns and taverns. There were whaling captains in Vineyard Haven, as in Edgartown, but the main orientation of the harbor throughout the Age of Sail was toward the coastal trade that passed through the Vineyard Sound.
As the village grew, some of the residents began to chaff at having to tell off-Islanders they lived in a hole and agitated for calling the place Tisbury Harbor, but in 1871 the voters opted for the more scenic name of Vineyard Haven. Unfortunately, most of the scenic part of town burned to the ground in the Great Fire of 1883, which started in a harness shop and in six hours destroyed thirty-two homes, twenty-six stores, twelve barns, two stables and a church. All the other towns of the Island came to the aid of Tisbury, and the waterfront was rebuilt with remarkable speed. But by that time the interests of the maritime residents of the harbor area had diverged from those of the more agricultural population Tisbury, to the point that the rural residents up Island, in particular, wanted a divorce. When the split came in 1892, the community around the harbor kept the original name and the up Island town became West Tisbury.
Vineyard Haven is still the hardest working harbor on the Island, the port of entry for virtually everything imported from off-Island. It’s also a famous center of wooden boat building and maintenance, with the tall ships of the Black Dog empire usually at anchor in the harbor and the legendary boat yard of Gannon and Benjamin turning out the worlds most beautiful handmade sailing yachts.
The summer scene is historically the most eclectic on the Island, ranging from the surprisingly stuffy “tennis whites only” crowd at West Chop, to the incoming hoards of day-trippers, to the old guard literary lions of Main Street, to the regular year-rounders who, believe it or not, also love summer on the Vineyard.
Land Area: 6.6 sq mi (17.0 km2)
Water Area: 12.6 sq mi (32.6 km2)