During pre-Columbian times, the area was inhabited by Wampanoag natives, who lived in settlements across southeastern Massachusetts and Rhode Island. The history of European presence in Vineyard Haven goes back quite far. The Englishman Bartholomew Gosnold first sailed to the island in 1602, but it was Thomas Mayhew who purchased Martha’s Vineyard from the Wampanoag, along with Nantucket and the nearby Elizabeth Islands. His son, also named Thomas, began the first settlement on Martha’s Vineyard in 1642 at present-day Edgartown.

The community of Vineyard Haven is a part of the town of Tisbury, which was settled in 1660 and incorporated in 1671, only a few decades after the Puritans first settled near Plymouth Rock, further north on the Massachusetts coast.

In the 1800s, Martha’s Vineyard and primarily its port of Holmes Hole, came to prominence as a premier whaling location, but demand for whale blubber and oil declined when petroleum was discovered as a cheaper source of fuel in the second half of the century. However, around this time, the tourism industry began to develop on the island (primarily at Woods Hole), and many wealthy vacationers purchased second homes on Martha’s Vineyard. Today, the island is famous for being frequented by many celebrities such as the Clintons, the Kennedy family, Bill Gates and a variety of prominent senators and actors.