The last railway line built in the city was the Canadian Northern Railway linking Toronto to Parry Sound in 1906. It came down the west side of the Don River and its two yards were located at Cherry Street and in the Rosedale valley. Complaints about the noise and dirt from the valley caused the railway to move that yard to Leaside in 1919.

In the early part of the century, railway traffic on the Esplanade had become increasingly heavy with numerous freight trains and at least 48 passenger trains every day. All these trains ran at ground level presenting a serious hazard to pedestrians and traffic. The Grand Trunk and Canadian Pacific railways formed a joint company, the Toronto Terminals Railway Company (TTR), to regulate rail traffic along the waterfront and in Union Station. Several railways were also reorganized, and Canadian National Railway (CNR) was formed, acquiring Canadian Northern Railway in 1919 and Grand Trunk Railway in 1923.

During the 1920s, the railways along the waterfront underwent a massive change. The Prince of Wales opened the fourth Union Station in August 1927, although the track area was not yet finished. In this new station, the main passenger hall had a high vaulted ceiling and the train sheds low ceilings, in contrast to the earlier Union Stations where ceilings in the passenger areas were low and lofty in the train sheds. Work also began on the enormous viaduct project to separate the railway tracks from the street traffic. The tracks were raised 18 feet above ground level and all the major streets were bridged. Track was laid farther south on the edge of the waterfront, and the harbour landfill was increased yet again to provide new industrial sites. Both CPR and CNR reorganized and expanded their yards. CPR built the John Street roundhouse and yards in 1927-28, just south of the Sky Dome today.

The Depression caused a large reduction in the amount of passenger railway traffic between Toronto, Montreal and Ottawa. CNR and CPR began to pool their trains between Toronto and Ottawa in 1933, and between Toronto and Montreal in 1934.

King George VI and Queen Elizabeth made a trans-Canada tour by train in 1939, the first visit to Canada by a reigning monarch. They came to Union Station on June 6, 1939. Three months later Canada would be at war. The Second World War created a surge in passenger travel, and the trains had to be lengthened and run in sections.

Railways were extensively and heavily used during the Second World War to transport troops and military supplies. By the end of the war, tracks, trains and cars were old and worn out. Steam engines were gradually replaced by diesels. The Canadian National Railway experimented with diesel engines in 1928, but only started using them as yard switchers in 1946. As the railways changed to diesels, roundhouses were no longer necessary. CNR closed the Danforth Yard and transferred to its marshalling yards at Mimico.

However, the railway era was passing. By the 1950s, the public's fondness for the ease and mobility of cars for personal travel, the use of trucks for freight, and of airplanes for long distance travel meant that the reliance on railways had dwindled significantly. Railways, although vital to the building of Toronto and indeed our country, remained an important but no longer dominant force.

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