Back as early as 1636, William Pynchon began to have personal and business relationships with the Quaboag Indians (whom the settlement is named after) that lasted 40 years.
In 1660, his son John took over business at his Springfield plantation and wanted to build a new plantation that was about halfway between Boston and Springfield, to shorten a long trip that was normally done by ship.
The nearest towns at the time were Springfield, a 25-mile journey through the wilderness, and Concord which was 44 miles away.
As more and more settlers came from all over Massachusetts Bay Colony, the town eventually became incorporated as the "Township of Brookfield".
Two years later though, the town was abandoned after it was ransacked by the Indians fighting for King Philip's War.