When colonists first lived in South Farms is unclear. Land deeds on the east side date to 1723, when local surveyors laid out the area's first east–west road. Also on the east end, and perhaps even earlier, a north–south road from Litchfield's Chestnut Hill ran down through the section that became known as The Pitch (so-called because the settlers "pitched", or drew lots, for land there). In 1724, the Connecticut Colony required settlers to build a fort, a log bulwark, on a hillside near the intersection of the old Woodbury (now Higbie) Road and present-day Benton Road. The work took them away from planting, diminished the year's harvest, and was consequently unpopular. The structure fell fairly rapidly into disrepair.