In 1640 settlers from the New Haven Colony purchased land from the Siwanoy Indians in the area now known as Old Greenwich. Shortly thereafter the English joined the Dutch in a dispute with the Siwanoys which resulted in their massacre. After the disappearance of most of the Indians the industrious newcomers carved out larger and larger land holdings on which to raise potatoes, grain, and fruit. Settlements grew along the shore from Stamford on the east to the Byram River on the west and north to the border with New York State. By 1730 the 50 square miles which comprise present day Greenwich were laid out. For its first 200 years the acquisition and cultivation of farm land was the major enterprise of residents, although grist mills signaled the beginnings of local industry and active shipping was conducted from the Mianus River. The relative calm of these years was broken by the Revolutionary War. Greenwich was a garrison Town which experienced occupation by both British and American armies as well as raids from irregulars.
The seven-year long war was fought on the roads and farms of Greenwich destroying homes, crops, and human lives.