The historic Stockbridge Railroad Station was built in 1893, replacing the original wooden structure, with funds partially furnished by the Laurel Hill Association, the nation’s first village improvement society. The association played an important role in the development of Stockbridge and helped create the town’s reputation as an attractive community. The association’s work to beautify the town encouraged the growth of tourism, including attracting wealthy cottagers who summered in Stockbridge and they received a handsome train station to greet them upon their arrival.

Built with beautiful blue dolomite stone, it was designed by architect Frank Waller in the English Gothic Revival style and used by the New York, New Haven, and Hartford Railroad until the early 1960's. Over the years, it was used for several commercial ventures, including a nightclub and was almost destroyed by a kitchen fire on July 22, 1965. It was purchased by Berkshire philanthropists Jane and Jack Fitzpatrick’s High Meadow Foundation in 1997 and subsequently restored as a railroad station. From 2003 until 2011, the station served as the BSRM's southern terminus for its train rides and was the site of many memorable special events.