This chapter introduces the history of the Sylvester Manor Project. It emphasizes the importance of the interdisciplinary approach employed during the project and the overall goals of the investigations. A discussion of pluralistic space and its importance as a central theme of the investigations is also presented. This is followed by a discussion of the Native American history of Shelter Island and its European colonization with particular attention given to the initial establishment of Sylvester Manor as a provisioning plantation, its connections to two large sugar plantations on Barbados, and its subsequent transformation into a commercial estate.