The square is named for John Winthrop (1587/1588–1649), an English Puritan lawyer and one of the leading figures in founding the Massachusetts Bay Colony, the second major settlement in New England following Plymouth Colony.

[1] Situated in front of the 1873-constructed One Winthrop Square,[2] the columns on the building's façade were used as the inspiration for the square's paving pattern, which contains strips of granite that "project in varied ways into the space to define entry, seating areas and diagonal circulation.

[5] The Atlantic Monthly had its Boston offices at 220 Devonshire Street in Winthrop Square in the 19th century.

[6] James R. Osgood and Company inherited The Atlantic Monthly and its office location.

[9] The square was home to a statue of Scottish poet Robert Burns for 44 years, having been moved from Boston's Back Bay Fens in 1975.