If completed, the Danbury and Norwalk Railroad would provide a route from Litchfield County to the Sound that bypassed Bridgeport.

[1] Protective of Bridgeport's position as a hub for Housatonic Valley trade, they decided to build a railroad of their own before the Danbury and Norwalk could be completed.

[1] 23 year old William Henry Noble (a future Union Army general[2]) drafted two charters for the railroad, one for the businessmen, and one for the city of Bridgeport itself.

[7] The extension became part of the Housatonic's main line, while the original alignment to the New York border provided an alternative route for freight trains.

Considered redundant, the original Housatonic main line was abandoned between Bridgeport and Stepney in 1940, as was duplicate trackage between Brookfield Junction and Hawleyville.

[8] The remainder of the original main line south of Botsford was abandoned in 1963, and the connection between West Stockbridge and the New York border followed the next year.

The last remaining passenger train on the line was discontinued in 1971 upon the formation of Amtrak, and freight service heavily declined as well, but Penn Central did not abandon anymore of the Housatonic system.

[8] When government-formed Conrail took over from Penn Central in 1976, it cut the line in two, abandoning the infrequently used 35 miles (56 km) between Canaan and New Milford.