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. 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.
Disputed information: In 1889 a branch of the line from New Preston was extended four miles (6 km) to Lake Wauramaug. This line carried vacationing passengers in the summer time and also helped to distribute ice from icehouses throughout the year.
In 1892 the NYNH&H leased the Hawleyville-Bethel branch to the Shepaug.
Stations and flag stops along the line from northeast to southwest with distances from Hawleyville included the following:
|Litchfield||38 mi (61.2 km)||Northeastern terminus and headquarters of the railroad|
|Bantam||33 mi (53.1 km)||The nearby lake supplied ice to urban markets in the days before refrigeration.|
|Morris||32 mi (51.5 km)||This location was also known as "Smoke Hollow".|
|Romford||Site of station is now a soccer field for the Rumsey Hall School which relocated here in 1949.|
|New Preston||Start of branch to Lake Wauramaug|
|Washington||24 mi (38.6 km)||The station was in the Washington Depot village in the Shepaug River valley.|
|Valley Station||Whistle stop for Holiday House (1893-1918)|
|Judd's Bridge||22 mi (35.4 km)|
|Roxbury||18 mi (29 km)|
|Roxbury Falls||Home of the Silicon Mills (quartzite powder factory) until it burned in 1908.|
|Shepaug||The small lean-to building was more of a whistle stop.|
|Hawleyville||0 mi (0 km)||Interchange with the Housatonic to Danbury, Bridgeport, and Pittsfield; D&N to Bethel|
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