1943 Map of Ossining

About this map

Sing Sing Prison stands prominently along the Hudson River shoreline in this mid-century view of Westchester County. The landscape is defined by the massive New Croton Reservoir and its associated Croton Dam, which dominate the northern half of the region. This era of development shows a significant concentration of religious and educational institutions, including the Maryknoll Seminary, Maryknoll Convent, and Briarcliff Junior College. Local transportation relies on the New York Central railroad and historical corridors like the Albany Post Road. The interior is dotted with private estates and recreational grounds such as the Sleepy Hollow Country Club and Briarcliff Country Club, interspersed with small crossroads like Millwood and Chappaqua. The topography reveals a transition from the riverfront heights of Ossining to the interior hills and numerous small glacial ponds and lakes.