My list of great songs of Canada, songs that capture the essence of Canada, are (in chronological order):

The Land of the Muskeg and the Shining Birch Tree by Wade Hemsworth
Four Strong Winds by Ian Tyson
Canadian Railroad Trilogy by Gordon Lightfoot
Northwest Passage by Stan Rogers
Out Past the Timberline by Murray McLauchlan.

I limited myself to one song per songwriter. Certainly there are others by each of those writers that could be on the list