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The territory now comprising the city of Somerville was first settled by Europeans in 1629 as part of Charlestown. In 1629, English surveyor Thomas Graves led a scouting party of 100 Puritans from the settlement of Salem to prepare the site for the Great Migration of Puritans from England. Graves was attracted to the narrow Mishawum Peninsula between the Charles and Mystic rivers, linked to the mainland at the present-day Sullivan Square. The area of earliest settlement was based at City Square on the peninsula, though the territory of Charlestown officially included all of what is now Somerville, as well as Medford, Everett, Malden, Stoneham, Melrose, Woburn, Burlington, and parts of Arlington and Cambridge. From that time until 1842, the area of present-day Somerville was referred to as “beyond the Neck” in reference to the thin spit of land, the Charlestown Neck, that connected it to the Charlestown Peninsula.

The first European settler in Somerville of whom there is any record was John Woolrich, an Indian trader who came from the Charlestown Peninsula in 1630, and settled near what is now Dane Street. Others soon followed Woolrich, locating in the vicinity of present-day Union Square. In 1639 colonists officially acquired the land in what is now Somerville from the Squaw Sachem of Mistick. The population continued to slowly increase, and by 1775 there were about 500 inhabitants scattered across the area. Otherwise, the area was mostly used as grazing and farmland. It was once known as the “Stinted Pasture” or “Cow Commons”, as early settlers of Charlestown had the right to pasture a certain number of cows in the area.

John Winthrop, the first colonial governor of the Massachusetts Bay Colony, was granted 600 acres (240 hectares) of land in the area in 1631. Named for the ten small knolls located on the property, Ten Hills Farm extended from the Cradock Bridge in present-day Medford Square to Convent Hill in East Somerville. Winthrop lived, planted, and raised cattle on the farm. It is also where he launched the first ship in Massachusetts, the “Blessing of the Bay”. Built for trading purposes in the early 1630s, it was soon armed for use as a patrol boat for the New England coast. It is seen as a precursor to the United States Navy. The “Ten Hills” neighborhood, located in the northeastern part of the city, has retained the name for over 300 years. New research has found that less than a decade after John Winthrop moved to the farm in 1631, there were enslaved Native American prisoners of war on the property. Each successive owner of Ten Hills Farm would depend upon slavery’s profits until the 1780s, when Massachusetts abolished the practice.