This paper examines the dialectology of eastern New York State. Data are considered from twelve cities and villages bridging the gap between the Inland North dialect region (home to the Northern Cities Shift [NCS]) and the Western New England region. Communities are classified as belonging to the Inland North “core,” the Inland North “fringe,” or a non–Inland North region. The settlement history of these communities is used to explain the boundaries between the dialect regions; presence of the NCS is found to correlate well with heavy migration from southwestern New England early in a community's history. Looking in detail at the different distributions of the individual sound changes involved in the NCS across the dialect regions established in this paper makes it possible to posit a reconstructed early history for the NCS and make hypotheses about the phonological character of the different sound changes.