Winthrop is a town in Suffolk County, Massachusetts, United States. The population was 19,316 at the 2020 census. Winthrop is an ocean-side suburban community in Greater Boston situated at the north entrance to Boston Harbor, close to Logan International Airport. It is located on a peninsula, 1.6 square miles (4.2 km²) in area, connected to Revere by a narrow isthmus and to East Boston by a bridge over the harbor inlet to the Belle Isle Marsh Reservation.

Settled in 1630, Winthrop is one of the oldest communities in the United States. It is also one of the smallest and most densely populated municipalities in Massachusetts. It is one of the four cities that compose Suffolk County (the others are Boston, Revere, and Chelsea). It is the southernmost part of the North Shore, with a 7-mile (11 km) shoreline that provides views of the Atlantic Ocean to the east and of the Boston skyline to the west.

In 2005, the Town of Winthrop voted to change its governance from a representative town meeting adopted in 1920 to a council-manager form of government. Under Massachusetts law, as of 2006 when the new Town Charter took effect, Winthrop became de jure a city. However, it is one of thirteen cities in Massachusetts that chose to remain known as a ‘town.’

Winthrop was settled in 1630 by English Puritan colonists as Pulling Point, so named because the tides made hard pulling for boatmen. The present town is named after John Winthrop (1587–1649), second governor of the Massachusetts Bay Colony and an English Puritan leader. On April 8, 1630, Winthrop departed from the Isle of Wight, England on the ship Arbella, arriving in Salem in June where he was met by John Endecott, the first governor of the colony. John Winthrop served as governor for twelve of the colony’s first twenty years of existence. It was he who decided to base the colony at the Shawmut Peninsula, where he and other colonists founded what is now the City of Boston.

Originally part of an area called Winnisimmet by the native Massachusett tribe, Pullen Poynt was annexed by the Town of Boston in 1632 and was used as a grazing area. In 1637, it was divided into fifteen parcels of land that were given by Governor Winthrop to prominent men in Boston with the stipulation that each must erect a building on his land within two years. Few, if any, of these men ever lived on these parcels of land, but their farms prospered. One of these early houses, the Deane Winthrop House, was the home of Governor Winthrop’s youngest son, Deane Winthrop, who lived there until his death in 1704. This house is still standing and is also the oldest continually occupied home in the United States. Although occupied, it is also open to the public at select times. The house is maintained by the Winthrop Improvement and Historical Association.

In 1739, what is now Chelsea, Revere, and Winthrop, withdrew from Boston due to governmental control disputes and became the Town of Chelsea. In 1775, residents of the Town of Chelsea played a key role in the Battle of Chelsea Creek of the American Revolutionary War. Again, the desire for more local control resulted in Revere and Winthrop seceding from Chelsea in 1846 to become North Chelsea. Shortly thereafter, in 1852, Winthrop was incorporated as a town in its own right with a Board of Selectmen and Open Town Meeting form of government. In 1920, Winthrop was the second town in the Commonwealth of Massachusetts to apply for and receive a Charter for a Representative Town Meeting, which continued to 2006.

As noted above, Winthrop adopted a home rule charter in 2005 with a council-manager form of government and is no longer governed by a representative town meeting. It is now legally a city, but chooses to be known as a town that has a city form of government. The new Town Charter, which took effect in 2006, was passed in a special election. The Board of Selectmen and Town Meeting were abolished, and legislative powers were vested in an elected Town Council. Executive power, largely ceremonial, resides in the Council President, who is popularly elected. An appointed Town Manager serves as the head of administrative services.