The South and North County Trailways and the Putnam Trail are what remain of the New York Central Railroad's Putnam Division, New York City's first rail link to Boston by way of a connection in Brewster. The South County Trailway is located on the right-of-way of the former railroad; sections of the North County Trailway are constructed on land that was formerly the right-of-way for the railroad. With the exception of certain segments used for roadway construction, most of the remaining right-of-way north of Eastview in the Town of Mount Pleasant has been preserved.

Conceived in 1871, the Putnam Railroad was proposed as part of an inland rail system linking New York City to Boston and Montreal via Brewster, Danbury, and Hartford. This plan failed because of competition with other lines, related financial problems, and the panic of 1873. The New York City & Northern Railroad purchased the right-of-way from the bankrupt New York, Boston & Montreal and, in 1879 and 1880, constructed a new commuter line through Westchester and Putnam counties from Brewster to High Bridge in the Bronx. There, passengers transferred across the platform to Hudson line trains. Daily service began in December 1880.

In 1881, a connection across the Harlem River north of Macombs Dam Bridge on the Putnam Bridge allowed commuters to transfer at 155th Street and Eighth Avenue to the Sixth and Ninth Avenue Els which ran to downtown Manhattan. Financial failure forced the line to be leased to the New York Central in 1895. In 1913, it was formally merged into the New York Central. When the IRT system extended its Ninth Avenue El into the Bronx in 1916, the IRT leased the Putnam Bridge and the Putnam Division terminated at Sedgwick Avenue. The Putnam Divisionís backwoods nature and the Bronx transfers never allowed it to grow like the Harlem and Hudson lines.

Although used primarily by passenger trains, the line also provided freight service from rural northern Westchester and Putnam Counties to New York City from 1881 to 1958. In addition to milk and farm products, the Putnam Railroad carried iron ore from mining centers such as the Tilly Foster mines on the border of Westchester and Putnam Counties. Freight service continued to operate occasionally on lower portions of the line (Elmsford and south), but retracted southward until it eventually disappeared entirely. Sporadic freight service on the Putnam line below Van Cortlandt Park continued into the early 1990s.

"All mileage is subject to argument" accurately applies to the Putnam line. Already noted are the changes to the southern terminus. In the early twentieth century, Eastview marked the point where the line veered westward (on todayís Tarrytown Lakes Trailway), stopping at Tarrytown Heights, Tower Hill, and Pocantico Hills before continuing to Briarcliff Manor. Because of the railroad, Pocantico Hills became a thriving business community. It consisted of two livery stables, two grocery stores, a butcher shop, two apartment houses, a post office, and two hotels.

In 1930, John D. Rockefeller, Jr., who found the noise and dirt of the trains objectionable (he and his guests wore goggles while playing golf), paid to move the railroad to the eastern edge of his estate at Pocantico Hills. As well as moving the railroad, Rockefeller paid to relocate about 150 families and the Christian Brothers winery. While the new route cut the distance between Eastview and Briarcliff Manor by three miles, fewer people used it and it generated no freight traffic. Mileposts on the northern portion of the line are inaccurate because of the shortening of the route.

Characteristic of this line's stations is a residential style of architecture reflecting the buildings in the area where the stations were located. Stations in more urban Southern Westchester were constructed of stone while those to the north were made of wood. Many depots used kerosene lamps until 1952. Flag stops like Woodlands Lake and Worthington were merely open shelters.

Many factors contributed to the death of the Putnam Line including construction of the Saw Mill River Parkway, the New York State Thruway, and the decline of Saturday commuting.

Slowly but surely, starting in the late 1970s, Westchester and Putnam Counties have converted stretches of the old Putnam Division line of the New York Central Railroad into three paved multiuse paths. Many homeowners adjacent to the railroad right-of-way were originally concerned their property values would decline and that public access would make their neighborhoods less safe. Instead, homeowners have built access points to the trail rather than fences. Utilizing railroad rights-of-way from the nineteenth century (the Maybrook line, from Danbury through Dykemans to Beacon), there are plans to connect the trails north with Dutchess County's rails-to-trails initiatives and east with a Connecticut project.

Compiled from signs along Westchester's South and North County Trails and from other sources, Summer, 2005