Exchange for Canadian funds in advance. Don't waste time with only 24 hours looking for a bank or money exchange after you arrive. Definitely have some Canadian funds on hand. Our dollar is undervalued compared to the US. So if a taxi charges you $20 Canadian on the meter and you pay with $20 US, you are overpaying -- even if the driver claims to give you a fair exchange rate, odds are you are overpaying. Taxi drivers don't like taking credit cards, even though by law they are supposed to. Cash is easier to pay for taxis. You don't need a chip credit or debit card at Canadian businesses. They will swipe, print and have you sign the old fashioned way. Chip and PIN are a convenience factor, not a requirement. If you run out of Canadian cash, if you are in a city with lots of US tourism eg. Vancouver, American funds would be accepted at most businesses. But again, you may not get the most favourable exchange.
Foods - Tim Horton's is overrated. But if you want to try it and seem like a "Local", ask for a "double-double". That's shorthand for double cream and double sugar. But their doughnuts are premade and frozen, then rebaked in the store - nothing special. I'd take a Krispy Kreme anytime. There are regional specialties - what part of Canada are you going to? Poutine (french fries, gravy, melted cheese curds) are definitely a favorite. What I suggest is going to TripAdvisor, looking up the city you are going to, and check out the top rated restaurants. This is what we do when travelling in the US or Canada. Don't go to chains you can go to at home e.g. McDonald's.
Vancouver has lots of great independent restaurants. Maritimes (east coast provinces) known for seafood. Montreal and Quebec city - French food, smoked meat, poutine. But lots of great ethnic food choices if you like international. Buy a bottle of maple syrup to bring home. Hope this helps.