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I am indeed in streetsville, I just go to Montreal often on business.
I would definately try and catch some of the Just for Laughs festival, its awesome. For dinner definately try Weinstein & Gavino's on Crescent Street - the Veal Chop is amazing. For smoked meat I always hit Rubens on St. Catherines. They also have amazing strawberry cheesecake. After dinner have a beer at the Montreal Ballet.
A wicked jazz bar is 'Biddles' Its on Aylmer I think.
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"It is impossible to obtain a conviction for sodomy from an English jury. Half of them don't believe that it can physically be done, and the other half are doing it."
Winston Churchill
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