Although the New York & Harlem Railroad traversed the Pawling community as early as the late 1840s, the town did not receive a dedicated passenger station until the construction of one by the New York Central & Hudson River Railroad in 1881.

[dubious – discuss] The station was one of the stops on the Harlem Line for trains such as the Berkshire Hills Express, offering limited-stop service between New York City and destinations in the Berkshires region, including Pittsfield and North Adams, Massachusetts.

PC's ongoing financial difficulties throughout the 1970s led to the transfer of its commuter services to the Metropolitan Transportation Authority (MTA), which continued operations through the formation of Conrail in 1976.

[10] The station consists of a four-car-long high-level side platform to the east of the track.

[11]: 15 Media related to Pawling (Metro-North station) at Wikimedia Commons