Shepaug, Litchfield and Northern Railroad

"Shepaug" in the railroad's name derived from the name of the Shepaug River, followed by most of the line, which in turn was a Mohegan name that meant "rocky water".[4]

The railroad was chartered in 1866 or 1868 and opened for operation on December 7, 1871 as the Shepaug Valley Railroad.[2][5] J. Deming Perkins was the company's first president. Henry R. Colt was the treasurer and Edwin McNeill was the superintendent.[5] Regular service to Litchfield started by January 11, 1872.[5] Due to the expense of building and maintaining the line through rocky rural terrain the railroad suffered low profitability throughout its existence. To help pay creditors it was reorganized as the Shepaug Railroad in 1873 and was again reorganized as the Shepaug, Litchfield and Northern (or SL&N) on May 9, 1887.[2]

The first three 30–ton 4-4-0 steam locomotives to run on the Shepaug line were from the Rogers Locomotive and Machine Works of Paterson, New Jersey named Shepaug, Weatinaug, and Waramaug.[5][6] In addition to passenger traffic the railroad shipped freight. Gail Borden's condensed milk business had started operation in the Burrville section of Torrington in the 1860s. Thanks to strong sales during the civil war that business was quite profitable and was looking to expand in the 1870s. A new Borden creamery was built and started shipping dairy products out of Washington Depot soon after the start of operations on the SL&N. Other significant freight shippers included stone quarries near Roxbury and New Preston (marble and granite)[5] and ice cut from Bantam Lake.[6]

At first, the SL&N would run two trains down from Litchfield toward Hawleyville with two return trains later in the day each weekday.[7] A single passenger and a separate freight train ran on Saturdays. The need to get milk as fresh as possible to New York City markets led to runs of a Sunday "milk train". At first the milk was delivered to Hawleyville to be picked up by the Housatonic and then carried to Bridgeport and on to New York. Eventually the creamery at Hawleyville was closed as was the Hawleyville branch, by which time the milk train ran through Danbury to South Norwalk.[8]

In 1872, the railroad reached an agreement with the Danbury and Norwalk Railroad to operate trains on that company's newly constructed 6-mile (9.7 km) Hawleyville Branch to Bethel. Eventually the SL&N would run trains from Litchfield down to South Norwalk for connection with the New Haven or to Wilson's Point for ferry service connection to either New York or to Oyster Bay on Long Island.[9]

On July 1, 1898, the New Haven Railroad leased the Shepaug, Litchfield and Northern from the Housatonic and operated it as its Litchfield Branch until business weakened in the first half of the 20th century. The Borden Creamery in Washington was closed down in 1928.[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.[11] The ICC granted permission to abandon the line in 1948 which is when freight service stopped on the line.[11] In 1947 and 1948 the line finally saw the arrival of more modern diesel-electric locomotives for freight hauling, but their use was very short lived.[6] In 1949 the gandy dancers who had maintained the line pulled up the rails and ties as part of the abandonment.[6]

The Shepaug was renowned for its labyrinthine route. It was said that the line took 32 miles (51 km) of track to travel a distance of only 18 miles (29 km) as the crow flies. A 235 ft (72 m) long curved tunnel was cut through rock southwest of Washington Depot that still exists along a hiking trail.[12] There were reputed to be 192 curves along the line from Litchfield to Hawleyville or about six per mile.

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

In 1889 a branch of the line from New Preston was extended four miles (6.4 km) to Lake Wauramaug.[13] This line carried vacationing passengers in the summer time and also helped to distribute ice from icehouses throughout the year.[13]

In 1892 the NYNH&H leased the Hawleyville-Bethel branch to the Shepaug.[7]

Stations and flag stops along the line from northeast to southwest with distances from Hawleyville included the following:[7]