Music can define a destination. Two Canadian Broadcasting Corporation (CBC) radio shows compiled playlists of essential Canadian music which you may wish to download to your iPod to enjoy before or during your visit.

50 Tracks: The Canadian Version 

 In 2005, the summer series 50 Tracks: The Canadian Version chose a playlist of the 50 most essential songs in Canadian pop music history based on suggestions by panelists and listeners.Here are the top 10 choices:

 Ian and Sylvia (Tyson)   "Four Strong Winds"
 Barenaked Ladies  "If I had $1,000,000"
 Neil Young  "Heart of Gold"
 Stan Rogers  "Northwest Passage"
 The Guess Who  "American Woman"
 Gordon Lightfoot  "Canadian Railroad Trilogy"
 Joni Mitchell  "Both Sides Now"
 Leonard Cohen  "Suzanne"
  Joni Mitchell  "Big Yellow Taxi"
 Gordon Lightfoot  "Early Morning Rain"

Wikipedia has the complete list.

Obama's Playlist

 In the fall of 2008, after the election of U.S. President Barack Obama, 49 songs were selected  by CBC listeners and panelists as an "inauguration gift". The musical selections were meant to both entertain and educate the president-elect. This playlist (formally called 49 Tracks From North of the 49th Parallel) featured a variety of genres; here are the top picks from each group:

 English Rock Pop Folk etc.

 Rush     "Closer to the Heart" 
 Gordon Lightfoot     "Canadian Railroad Trilogy"
 k.d. lang     "Hallelujah"
 Leonard Cohen     "Democracy"
 Stan Rogers     "Northwest Passage"

Jazz

Oscar Peterson Trio      "Hymn to Freedom"
Michael Bublé     "Home"
Oscar Peterson     "Place St. Henri" (from Canadiana Suite)
Diana Krall     "Departure Bay"
Moe Kauffman     "Swingin' Shepherd Blues"

Classical

 Glenn Gould (performer)    Goldberg Variations 
 Measha Brueggergosman (performer)    I'm Going Up a Yonder
 Marjan Mozetich (composer)    Affairs of the Heart
 Ben Heppner (performer)    We’ll Gather Lilacs
 James Ehnes (performer)     Barber Violin Concerto

French Rock Pop Folk etc.

Gilles Vigneault     "Mon pays"
Malajube    "Montréal -40C" 
Marie-Jo Thério    "Évangéline"
Harmonium    "Pour un instant"
Daniel Lavoie    "J'ai quitté mon île"

The full list is on the CBC Radio 2 Blog.

And a couple of bonus tracks from Youtube

Julia Bentley & Andrew Gunadie - "Canadian Please"

Gene Pitney (1974) - Trans-Canada Highway (a song which was never released in North America but was a hit in Australia)