[4] The route served as a path to country homes of New Yorkers,[5] as well as to towns such as Canaan and New Milford in the transportation service-neglected northwest Connecticut, an area lacking Interstate highways or major airports.

[6] North from New Milford to Canaan, short of the Connecticut-Massachusetts state line, the route followed the Housatonic River.

In summer months the train made stops in Lenox, Massachusetts, the town hosting the Tanglewood Music Festival.

[7] By 1961 the Berkshire was cut to a Friday north-bound run; the Litchfield operated as a Sunday evening route from Pittsfield to New York.

[8] Finally, in 1968, the Berkshire name was dropped, and unnamed trains served the route until 1971 when the New Haven successor Penn Central discontinued service on the line.