The "Canadian Railroad Trilogy" is a song written, composed, and performed by Canadian singer-songwriter Gordon Lightfoot that describes the building of the trans-Canada Canadian Pacific Railway in the early 1880s.

This song 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.

While Lightfoot's song echoes the optimism of the railroad age, it also chronicles the cost in sweat and blood of building "an iron road runnin' from the sea to the sea." The slow middle section of the song is especially poignant, vividly describing the efforts and sorrows of the nameless and forgotten "navvies," whose manual labour actually built the railway.

Session personnel for the 1967 recording were: Gordon Lightfoot (12-string), Red Shea (Lead acoustic guitar), John Stockfish (Fender Bass), and Charlie McCoy (Harmonica).

Lightfoot re-recorded the track on his 1975 compilation album, Gord's Gold, with full orchestration (arranged by Lee Holdridge). A live version also appears on two of his live albums, first on his 1969 album Sunday Concert and again on the 2012 release All Live, which consists of songs recorded during the live concerts Lightfoot gave at Toronto's Massey Hall between 1998 and 2001.

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