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Don't hang out downtown - it's a central place to stay but a bit ordinary. If you want to go to the "hip" neighbourhoods go to Mile End, Jean Talon and the Plateau.
For Plateau, had a good meal at L'Express and Le 4e Mur for drinks afterwards. Mile End has the two famous Bagel places and you can just walk around and check out hole-in-the-wall places for good eats.
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