John Endecott, regarded as one of the Fathers of New England, was the longest-serving governor of the Massachusetts Bay Colony, which became the Commonwealth of Massachusetts. He served a total of 16 years, including most of the last 15 years of his life. When not serving as governor, he was involved in other elected and appointed positions from 1628 to 1665 except for the single year of 1634.

The Massachusetts Bay Colony (1628–1691), more formally the Colony of Massachusetts Bay, was an English settlement on the east coast of North America around the Massachusetts Bay, one of the several colonies later reorganized as the Province of Massachusetts Bay. The lands of the settlement were in southern New England, with initial settlements on two natural harbors and surrounding land about 15.4 miles (24.8 km) apart—the areas around Salem and Boston, north of the previously established Plymouth Colony. The territory nominally administered by the Massachusetts Bay Colony covered much of central New England, including portions of Massachusetts, Maine, New Hampshire, and Connecticut.