Born and raised in Toronto. What type of food do you like? I'll give as many recommendations as I can!
@posner08. I'm not a picky eater food-wise. So when I travel for work I like to go where the locals go for casual dining since I'm on a budget.
Get a weekly newspaper "Now" or "The Grid" to see what's going on. Yonge street is really mainstream touristy. If you want more "local hangout," I'd suggest Queen West. Queen and Bathurst could be a good corner to start at and work your way west on Queen. The Drake Hotel and Gladstone Hotel are two places that draw a huge crowd and have live music. Lots of ethnic restaurants around if you want to go a bit cheaper for dinner and then "go out" afterwards. Also, College Street is good too.
Feel free to PM if you have any more specific questions.
Not that I have ever patronized such an establishment, but I am told that there are some cafes in Toronto where one can openly smoke Cannabis. So if that appeals to you, that's one of the special features in this city not found in the states (or elsewhere in Canada even except for Vancouver I think).
It's still technically illegal, but openly tolerated and perfectly "safe." They aren't allowed to sell it though, so it's BYOP. The only place that did get busted was caught selling. The most well-known one is Hot Box cafe in Kensington Market, which is the most "hippy" part of town (most of Toronto is more "hipster."
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