In the fall of 1639, Roger Ludlow, one of the founders of the colony of Connecticut, led a small group of men and a large herd of cattle to the shore of Long Island Sound. At a place known to the local Indians as Unquowa, they established a settlement that became known as Fairfield, named for the hundreds of acres of salt marsh that bordered the coast. The marsh provided a plentiful supply of feed for the livestock and abandoned Indian fields became the site of the settlers' first agricultural plots. In the intervening years between those early days of settlement and today, much has occurred to change the face of Fairfield. Yet the town continues to bear the imprint of those who came before us.
The local Indians were known as the Unquowas, for the area in which they lived, which is thought to mean "the place beyond". The Unquowas were a small clan of the Paugussett tribe, which was centered in southwestern Connecticut. By the time of Ludlow's settlement, the population of these Indians had been severely decimated by diseases introduced by the early explorers. They made little resistance to Ludlow's claim of all the land from the Saugatuck River in the west to the Stratford bounds (now Park Avenue) in the east and a day's march inland from the Sound - a distance of approximately twelve miles.
The founding of Fairfield was not without conflict, however. Roger Ludlow had first seen this area in 1637 when as one of a band of settler-soldiers, he had pursued a group of Pequot Indians to a swamp in Southport. There, the Pequots made a last stand in a brief but bloody war caused by their resistance to settlers expansion into the Pequot's territory in eastern Connecticut. The battle is commemorated by a monument on the Post Road in Southport.
Although few seventeenth-century dwellings remain standing in Fairfield, evidence of the early settlement of the town is visible to this day in the form of the town's road system. Roger Ludlow laid out a grid for his new town; today's Post Road, Old Post Road, Beach Road, and South Benson Road, centered on the Meeting House Green, now the Town Green. On these streets the settlers built their homesteads and the Meeting House, seat of government and place of worship. Around the village was a cluster of common fields where the early settlers raised their crops, grazed livestock and cut timber. Oldfield Road, Benson Road and Unquowa Road were once farm lanes which gave access to these fields. Fairfield prospered during its first century. Surplus farm products were traded for imported goods. Black Rock Harbor, now part of the City of Bridgeport, became the town's leading port. There, ships were laden with wheat, flax, timber and livestock from the farms and sailed to Boston, New York and harbors as far away as the West Indies. They returned with needed goods such as nails to build their houses, textiles for clothing and furnishings, and molasses to be made into rum. The shipyards and wharves provided employment for many, including slaves. During the colonial period, Fairfield had one of the highest populations of blacks in Connecticut, almost all of whom were enslaved.Colonial Towns of Connecticut Links