In 1602 Bartholomew Gosnold made landfall at Cuttyhunk, and gave the Elizabeth Islands group its name. Captain Kidd anchored in one of Gosnold's harbors in 1699 just before he was captured for piracy. Major General Wait Steel Winthrop and James Bowdoin of Boston developed their property there as a country estate, stocking it with deer and turkeys. In 1759, one of the earliest lighthouses was built on Naushon at Tarpaulin Cove and six years later, a light was built on Cuttyhunk to warn of the disastrous reefs near the islands.

Residents of the islands fought for almost two centuries to become independent of the Town of Chilmark to which they were attached. In 1863, the 16 legal voters of Gosnold claimed they were not being fairly represented and finally succeeded in getting permission to establish an autonomous town.

The islands in the chain include Cuttyhunk, Penikese, Nashawena, Pasque, Naushon and Nonamessett, all of which are privately-owned, except for Cuttyhunk.

Today, Gosnold provides summer homes to some and year-round homes to a handful, as one of the smallest communities in the Commonwealth.