For many years, the line had significant curvature throughout its length, a result of the rugged local topography, which earned it the moniker, "Hellish Slow & Wobbly".

The Nova Scotia Central Railway (NSCR) had opened its line between Middleton in the Annapolis Valley and Lunenburg, by way of Bridgewater, on December 23, 1889.

In 1893, the Coast Railway Company of Nova Scotia was incorporated under a charter to build a narrow gauge line between Yarmouth and Lockeport, by way of Barrington and Shelburne.

Under the CNR, the H&SW trackage saw significant infrastructure improvements to ballast, drainage, sleeper ties, rails, switches and bridges.

The project excavated a massive railway cut across the isthmus of the Halifax Peninsula, which affected the H&SW tracks that connected with the ICR mainline near Africville.

In 1921, the Halifax end of the H&SW was shifted to join the new alignment in the rock cut by constructing what became known as "Southwestern Junction" in the community of Fairview, adjacent to a large new roundhouse complex.

In the years before the domination of publicly funded highways, the H&SW formed a critical transportation link between the various communities, as well as steam ship connections at Yarmouth (to Boston and New York) and Halifax (to Europe).

The construction of the large Bowater Mersey Paper Company Limited mill at Brooklyn in 1929 led to more traffic from the Liverpool area.

Shipyards in Liverpool and Shelburne lent some traffic, as did various saw mills and logging operations at locations between Yarmouth and Halifax, between Bridgewater and Middleton/Bridgetown and between New Germany and Caledonia.

CN's former H&SW lines on Nova Scotia's South Shore and in the Annapolis Valley were proving uneconomic by the early 1980s, even for freight service.

In the early 1990s, even that trackage was eliminated, as Michelin began to use trucks to service its plant and CN's last remaining customer in Lunenburg County was the forest products company at East River.

In 1993 the former H&SW trackage was abandoned west of Halifax's Lakeside Industrial Park, leaving only a 7-mile spur as the last reminder of this once important railway network in southern Nova Scotia.

In 2006, as part of its "Three-Year Rail Network Plan", CN declared its intention to discontinue service on the Chester Spur, this being the last remaining portion of the original H&SW trackage.