An early map of the area (dated 1637) from the papers of the family of John Winthrop includes some of this neighborhood and the adjacent Ten Hills section.
[7] The "Midnight Ride" of Paul Revere crossed over Winter Hill, and is re-enacted each year as part of the Patriots' Day festivities in the Boston area.
[8] An apartment in the Langmaid Terrace building on Winter Hill at 365 Broadway Avenue was the home of Barack Obama between 1988 and 1991 while he was a student at Harvard Law School.
[9] By the 21st century, Winter Hill featured a mix of restored homes and aging triple deckers, replete with china gnomes and bathtub Virgin Marys.
The park has a large, colorful mural painted behind the public swimming pool, and is home to a wide variety of sporting matches, especially soccer.