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The Early Years

In 1637, when the Connecticut General Court had declared war on the Pequot Indians and the Connecticut and Massachusetts militia were pursuing the remnants of the tribe along the Connecticut coast, Sergeant Thomas Tibbals “noticed the region about the mouth of the Wepawage that is today Milford.” From 1637 to 1697 there was war in one area or another with the Indians. History tells us that perhaps the most noteworthy of these was King Phillip’s War in which Major Robert Treat of Milford and “five companies of farmer-soldiers from Connecticut, including many from the North Milford area, nobly committed themselves.”

Peter Prudden played an important role in the first settlement of Milford. A native of Hertfordshire, England, Mr. Prudden first settled in the Massachusetts Bay Colony with some of his followers. Later he and those known as the “Prudden group” became a part of the New Haven Colony in 1638. During the summer Mr. Prudden went to Wethersfield to preach and attracted quite a following. At this time a movement started to found a separate colony made up of recruits from the Wethersfield group as well as the Hertfordshire group which was settled in New Haven.

On February 12, 1639, Edmund Tapp, William Fowler, Benjamin Fenn, Zachariah Whitman and Alexander Bryan journeyed approximately 10 miles west from the Colony of New Haven to the mouth of the Wepawaug to purchase a tract of land for their plantation. The present Town of Orange was originally a part of this tract which was purchased from Ansantawae, a sachem of the Paugusset Indians. The original tract included the towns now known as Milford and Orange as well as a portion of Woodbridge and it was “bounded by the East River, the Housatonic River on the west, the Sound on the south, including Poquahaug (Charles) Island and by the ‘two mile Indian path that goeth to Paugusset (Derby),’ on the north.” While the exact location of the “two mile” path has been questioned, historians believe that it was probably the present day road known as Fountain Street, which runs from New Haven through the lower part of Woodbridge. By following this west, it meets with Two-Mile Brook and from this point to the Housatonic River, the brook serves as the boundary line. Historical writings on Connecticut reveal that the purchase price for this original tract was six coats, ten blankets, one kettle, twelve hatchets, twelve hoes, two dozen knives and a dozen small mirrors.

Immediately following the signing of the deed by both parties, the old English “twig and turf” ceremony took place. Ansantawae was handed a piece of turf and a twig, which he in turn thrust the twig into the turf and returned it to the purchasers of the tract. By this act he signified that the Indians relinquished the land noted in the deed and everything growing upon it. At the time the Paugusset Indians were constantly harassed by the Mohawks and they hoped that by selling Wepawaug land that they might enlist the protection of the English.

Turkey Hill Reservation

By 1665 however, Chief Ansantawae and the members of his tribe had sold all of their property and therefore were unable to hunt or fish. The Town of Milford allowed them to settle on land at Turkey Hill overlooking the Housatonic River. Perhaps this was the forerunner of later Indian reservations throughout the United States.

Turkey Hill, which is a part of Orange, is just one of the seven hill areas located in the town. The others are Grassy Hill, George’s Cellar Hill, Indian Hill, Chestnut Ridge, Marsh Hill and Cemetery Hill.

First Settlement

Land in the area now known as Orange was surveyed and laid out in 1687. It was sometime after 1700, however, before a permanent settlement was first made in the High Plains area by Richard Bryan,