The original Housatonic Railroad was chartered in 1836 and was acquired by the New York, New Haven & Hartford Railroad in 1892. At that time, the railroad was 175 miles long, with 60 passenger depots. Though the last passenger train ran on April 30, 1971, that
may soon change
. A portion of the railroad was then land-banked until 1983 when the line from Canaan to New Milford, Connecticut was reopened and the Housatonic Railroad name was used again. The railroad expanded to Pittsfield, MA in 1991 and expanded again in 1992 to include the line from Derby, Connecticut to Beacon, New York. The railroad now consists of 161 miles of rail lines devoted to freight transportation.