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The "Canadian Railroad Trilogy" was commissioned from Lightfoot by the CBC for a special broadcast on January 1, 1967, to start Canada's Centennial year. It took him three days to write the work. It appeared on Lightfoot's The Way I Feel album later in the same year along with the song "Crossroads," a shorter song of similar theme. The structure of the song, with a slow tempo section in the middle and faster paced sections at the beginning and end, was patterned more or less opposite to Gibson's and Camp's "Civil War Trilogy," famously recorded by The Limeliters on the 1963 live album Our Men In San Francisco. In the first section, the song picks up speed like a locomotive building up a head of steam.
According to Lightfoot, Pierre Berton said to him, "You know, Gord, you said as much in that song as I said in my book." Berton was referring to his two bestselling books about the building of the railway across Canada, The National Dream and The Last Spike.
In 2001, Gordon Lightfoot's "Canadian Railroad Trilogy" was honoured as one of the Canadian MasterWorks by the Audio-Visual Preservation Trust of Canada.