Chappaqua and Millwood had no less than three successive passenger stations each over the years. The first Chappaqua passenger station was in the Chappaqua Hotel, built about the same time as when the New York and Harlem Railroad (now the Harlem Division of the Metro North Transit System) was extended through the area in 1846. The hotel was located on Main Street (now lower King Street) right next to the tracks. A separate small freight station was erected nearby, just across the tracks.  

By the 1870s, the station had a site of its own, on what is now North Greeley Avenue, where Rite-Aid used to be. A frame building, it had all the customary components of a passenger station: a waiting room, a ticket window, and a baggage room. It remined in service for about three decades. 

By around 1900, the station had become too small for the growing population of Chappaqua. In 1901, a new site on Horace Greeley’s former farm was donated to New Castle by Greeley’s daughter, Gabrielle Greeley Clendenin, and her husband, The Reverend Dr. Frank M. Clendenin. The new stone station was completed and dedicated with great ceremony in 1902. Although it no longer serves railroad passengers, it is remains in use as a popular café.

Meanwhile, in 1881, the New York and Northern Railroad, later the Putnam Division of the New York Central, reached New Castle to the west. A small, standard station was erected a short distance away from the largest building in the neighborhood, the inn and tavern known as the Granite House. At that time, it belonged to the Merritt family, and the area was known as Merritt’s Corners. As a new community grew up around the station, the name changed to Millwood. 

            Within a few years, the original station burned and was temporarily replaced by a retired boxcar. In 1909 a more elaborate station was built in Briarcliff Manor, and its standard station was moved up the tracks to replace the original one in Millwood. As shown in this photo of about 1945, the old boxcar remined in service as a freight depot.

            The Putnam Division shut down in 1958. The former station was occupied by a succession of small businesses, but eventually became vacant, and was demolished in 2012. The former railroad tracks live on as a popular bike and pedestrian trail and the stop's history is remembered in the Station Place street name that memorializes its past.