Sustainable archaeological practice involves the efficient performance of archaeological work in areas affected by development interests. In urban settings, planning agencies have recognized that geoarchaeological strategies are time and cost efficient. Deep testing methods minimize footprints to generate stratigraphic models that inform on past native environments, subsequent landscape change, absolute chronology, and site formation. When coupled with background historic and environmental data, geoarchaeological probing supplements or even precludes the need for costly excavation. In this study, the Metropolitan Transportation Authority Capital Construction Company (MTACC) sponsored the drilling and detailed stratigraphic analysis of four deep borings in preparation for a new subway tunnel in New York City. A more expansive set of boring samples was taken by the MTACC for geotechnical purposes. Our stratigraphic construct facilitated “retrofitting” of the MTACC observations to develop a laterally extensive baseline sequence. An allostratigraphic model was developed for a ten-block length of the Upper East Side of Lower Manhattan on the strength of radiocarbon dates and ethnobotanic and malacological analyses. Finally, geographic information system (GIS) modeling generated a series of time slices chronicling the transformation of the project area from Late Glacial times through the area's prehistoric and historic past.