Like all historical events, the story of the Town of Southhampton and its relations with the Shinnecock did not start with the first arrival of immigrants. The chain of historical events that led to the eventful 1640 meeting upon Peconic Bay began long before that June day. This story began in 1496. This historical writing focuses principally upon the relationship between what historically became known as the Shinnecock Indians, the government of Great Britain and her colonial policies, the province and later state of New York, and most importantly, the proprietors and inhabitants of the Town of Southampton, Suffolk County, New York. One premise of this writing is that the Indian populations of eastern Long Island were not ignorant of the ways of the English settlers. Edward Howell's 1640 observation that the first Indian leader that the new arrivals spoke to was conversant, to a limited degree, in the language of the new arrivals is suggestive that acculturation had preceded their arrival. It will be shown that the political leadership of the Shinnecock had more than average knowledge of English culture, mores, and most importantly, land use and ownership practices at the time of first sustained contact. A second premise is that the relationship between the Town of Southampton and its Shinnecock neighbors was, on the whole, one of peaceful co-existence. Diagrams and maps enhance the text.