In 1660 the Connecticut Colonial Legislature sent Matthew Allyn and Samuel Willys down the Connecticut River from Hartford to purchase land from the Wangunk Indian Tribe at the place the English called 'Land of Thirty Mile Island'. The island, now known as Haddam Island was thought to be thirty miles from the mouth of the "Grate River" at Long Island Sound (it is only 17 miles from the mouth of river). In May 1662 the Englishmen finally purchased land comprising approximately 104 square miles and extending in six miles on each side of the river from the straits at "Pattyquonck" (now Chester) to the Mattabeseck-Mill River (now Middletown) across to the line of Chatham (now East Hampton). The English paid 30 coats (worth approximately $100) for the land from four Native American chiefs, two queens and others. The Native Americans did set aside some property for their own use including 40 acres at Cove Meadow (Chester) and Haddam Island as well reserving the right to hunt and fish where they pleased.
Originally there were two small settlements on the west bank of the river, the Town Plot was laid out along the southern end of what is presently Walkley Hill Road and extended to the old burying ground (Burial Yard at Thirty Mile Island Plantation) and the Lower Plantation was settled south of the Mill Creek in the area now known as Shailerville. Each proprietor was given a home lot and land for farming. There was also land set aside for a meetinghouse and ministers lot. In October 1668 town was incorporated and given the name Haddam after Much Hadham in England. Haddam had very little tillable agricultural land and the best farming land was located along the river. Early residents utilized all of the natural resources available to them including water, fish, timber and granite in order to survive. The Connecticut River was a major source of income and transportation for the first 200 years of the town existence. Shipyards were built along the river, while many other small tributaries provided waterpower for mills and eventually factories.
