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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 multiple portions of Boston by a bridge over the harbor inlet to the Belle Isle Marsh Reservation in the Neighborhood of East Boston, a shared border at the Boston Logan International Airport, and at Deer Island. 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 comprise 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.'

Massachusetts ( , MASS-ə-CHOO-sits, -⁠zits; Massachusett: Muhsachuweesut [məhswatʃəwiːsət]), officially the Commonwealth of Massachusetts, is a state in the New England region of the Northeastern United States. It borders the Atlantic Ocean and Gulf of Maine to its east, Connecticut and Rhode Island to its south, New Hampshire and Vermont to its north, and New York to its west. Massachusetts is the sixth-smallest state by land area. With over seven million residents as of 2020, it is the most populous state in New England, the 16th-most-populous in the country, and the third-most densely populated, after New Jersey and Rhode Island. The state's capital and most populous city, as well as its cultural and financial center, is Boston. Other major cities are Worcester, Springfield and Cambridge. Massachusetts is also home to the urban core of Greater Boston, the largest metropolitan area in New England and a region profoundly influential upon American history, academia, and the research economy. Originally dependent on agriculture, fishing, and trade, Massachusetts was transformed into a manufacturing center during the Industrial Revolution. During the 20th century, the state's economy shifted from manufacturing to services; and in the 21st century, Massachusetts has become the global leader in biotechnology, and also excels in artificial intelligence, engineering, higher education, finance, and maritime trade. Massachusetts was a site of early English colonization. The Plymouth Colony was founded in 1620 by the Pilgrims of the Mayflower. In 1630, the Massachusetts Bay Colony, taking its name from the Indigenous Massachusett people, also established settlements in Boston and Salem. In 1692, the town of Salem and surrounding areas experienced one of America's most infamous cases of mass hysteria, the Salem witch trials. In the late 18th century, Boston became known as the "Cradle of Liberty" for the agitation there that later led to the American Revolution. In 1777, General Henry Knox founded the Springfield Armory, which, during the Industrial Revolution, catalyzed numerous important technological advances, including interchangeable parts. In 1786, Shays' Rebellion, a populist revolt led by disaffected American Revolutionary War veterans, influenced the United States Constitutional Convention. In the 18th century, the Protestant First Great Awakening, which swept Britain and the Thirteen Colonies, originated from the pulpit of Northampton preacher Jonathan Edwards. Massachusetts has played a powerful scientific, commercial, and cultural role in U.S. history. Before the American Civil War, the state was a center for the abolitionist, temperance, and transcendentalist movements. In the late 19th century, the sports of basketball and volleyball were invented in the western Massachusetts cities of Springfield and Holyoke, respectively. Massachusetts has a reputation for social and political progressivism; becoming the only U.S. state with a right to shelter law, and the first U.S. state, and one of the earliest jurisdictions in the world, to legally recognize same-sex marriage. Boston is considered a hub of LGBT culture and activism in the United States. Prominent American political dynasties have hailed from the state, including the Adams and Kennedy families. Harvard University in Cambridge is the oldest institution of higher learning in the United States, with the largest financial endowment of any university in the world. The university has educated eight U.S. Presidents, while Harvard Law School has educated a contemporaneous majority of Justices of the U.S. Supreme Court. Kendall Square in Cambridge has been called "the most innovative square mile on the planet" for producing high concentrations of entrepreneurial start-ups and quality innovations since 2010. Both Harvard and MIT, also in Cambridge, are perennially ranked as either the most or among the most highly regarded academic institutions in the world. Massachusetts's public-school students place among the top tier in the world in academic performance. Massachusetts is the most educated and one of the most highly developed and wealthiest U.S. states, ranking first in the percentage of population 25 and over with either a bachelor's degree or advanced degree, first on both the American Human Development Index and the standard Human Development Index, first in per capita income, and as of 2023, first in median income. Consequently, Massachusetts typically ranks as the top U.S. state, as well as the most expensive state, for residents to live in.