[5] Due to the expense of building and maintaining the line through rocky rural terrain the railroad suffered low profitability throughout its existence.

Other significant freight shippers included stone quarries near Roxbury and New Preston (marble and granite)[5] and ice cut from Bantam Lake.

[10] Passenger service on the Shepaug Division was stopped by 1932[6] and the New Haven petitioned the Interstate Commerce Commission to abandon the line as a freight road in 1947.

A 235 ft (72 m) curved tunnel was cut through rock southwest of Washington Depot that still exists along a hiking trail.

A 428 ft (130 m) Brown truss type bridge carried the rails over the Housatonic River between the village of Shepaug and Hawleyville.

[7] Stations and flag stops along the line from northeast to southwest with distances from Hawleyville included:[7] In 1889 architect Ehrick Rossiter (1854-1941), an 1871 graduate of The Gunnery in Washington, Connecticut, purchased 100 acres (40 ha) along the Shepaug River to save it from logging.

In 1893 philanthropists Edward I. and Mary Lawrence McLane Van Ingen built Holiday House south of Washington Depot following plans drawn up by Rossiter.

Holiday House served as a country hotel or retreat for young working women from New York City.

In 1929 the Steep Rock Association trustees purchased the rounded oxbow encircled hill known as the Clam Shell and added it to the preserve.

Several kilometers of former SL&N track right of way form hiking and bridle trails within the Steep Rock Association preserves today.