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if somehow I was *forced* to live in a Canadian city again, i'd break down the three big ones this way (of course i am generalizing like a mofo, but that's the point of these threads right?):
Vancouver: if you want outdoor adventures, nothing else comes close
Montreal: lots of culture, everything is much more mom and pop, great people, even the most basic bars stay open till 4 am. and the jazz. ah, the jazz.
T-dot: definitely gets the most good music acts in the country, just behind van. if you are heavy into live acts, this is the place to be. also (no, i'm not a fan myself lol), but the 'broadway' musical scene is huge there too, my aunt goes up there ever year just for that alone.
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