[3]: 4 The Hudson River Railroad reached Ossining on September 29, 1849,[1] opening the village up to industrial development along the waterfront and allowing farmers inland to ship their produce to the markets of New York City.

These businesses gradually supplanted the boat builders and docks that had occupied the riverfront in the early 19th century.

In 1914 the New York Central Railroad, which the Hudson River had long been merged into, built a new station, the current building, in the Renaissance Revival style.

It was placed on metal stilts to allow Main Street to pass over the tracks, eliminating the grade crossing that had been part of the original station.

Penn Central's continuous financial despair throughout the 1970s forced them to turn over their commuter service to the Metropolitan Transportation Authority.