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A significant part of the early 1960s folk revival, the song is a melancholy reflection on a failing romantic relationship. The singer expresses a desire for a possible reunion in a new place in the future ("You could meet me if I sent you down the fare") but acknowledges the likelihood that the relationship is over ("But our good times are all gone/And I'm bound for moving on ..."). The song has a clear Canadian context and subtext, including an explicit mention of Alberta province as well as references to long, cold winters.
The song was a hit in Canada, making the top ten of the single charts there in October 1963.
In the United States, the song did not have the same initial chart success. Ian and Sylvia's single version (released on Vanguard 35021) entered the Cashbox magazine "Looking Ahead" chart in September 1963. It was then recorded by The Brothers Four in a version that "bubbled under" the Billboard Hot 100 in October 1963. Subsequently, it was released by Ian and Sylvia on an album of the same name released in the U.S. in April 1964.
To American rock music listeners, the most known recording comes by Neil Young from his 1978 album Comes a Time, with harmony vocals from Nicolette Larson. It has received significant airplay over album oriented rock and classic rock radio stations and has become part of Young's concert repertoire, including featured performances during Young's yearly appearances at Farm Aid benefit concerts.
This folk classic has been recorded by many artists beyond those already named, including Hank Snow, The Seekers, Judy Collins, the Chad Mitchell Trio, Bob Dylan, Marianne Faithfull, The Searchers, John Denver, The Kingston Trio, Trini Lopez, Waylon Jennings, Chad and Jeremy, The Wolfe Tones, The Tragically Hip, Joan Baez, Vanity Fare, Glenn Yarborough, Tony Rice, Johnny Cash, The Carter Family, Sarah McLachlan, David Wiffen, and Schooner Fare.
Additionally, it is sung on the last night of the Edmonton Folk Music Festival each year.
Ian and Sylvia sang the song together at the 50th anniversary of the Mariposa Folk Festival on July 11, 2010, in Orillia, Ontario. On April 5, 2013, a recording of the song by Ian Tyson was played during the funeral of former Alberta Premier Ralph Klein, as the honour guard brought his urn into the Jack Singer Concert Hall.
The song is also referenced in A Prayer for Owen Meany, the 1989 novel by John Irving that deals with Americans living near or across the Canadian border. The narrator remembers how the main character, Owen, loved to hear that song as sung by the character of Hester.