blogTO's Benjamin Boles describes, at length, Toronto's long history as a conservative and repressive community starting with Prohibition. Among other things, Boles demonstrates why an apparently common stereotype that Canadians are less conservative than Americans is, if not altogether wrong, not deeply grounded in history. More interesting things are afoot.
It's no secret that the nickname "Toronto The Good" is more a reference to the city's puritan goody-two-shoes reputation than a reference to just our benevolence. Even the New York Times knows that before Rob Ford we were most famous for being a bit boring. We might not have it as bad as Vancouver (which is officially Canada's "No Fun City," according to Wikipedia), but we're certainly nowhere near as much of a party town as Montreal, which was once known as Sin City, before Las Vegas claimed that crown.
To be fair, much of Toronto's lameness comes from the fact the city happens to be located in Ontario. The province's liquor laws are legendarily strict and often bizarre. Even before the sale of alcohol was prohibited in 1916, the only way to legally purchase booze previous to the ban was by prescription.
When prohibition was finally lifted in 1927, the authorities made sure that it was still quite difficult to buy a drink. The early LCBO stores required that you first obtained a license to buy booze, and then after that still had to fill out a variety of paperwork to purchase your beverages of choice. You could only buy one brand at a time, and also only one type of alcohol in one visit (not to mention quantities being severely restricted).
It wasn't until 1969 that you actually could walk into an LCBO and pick a bottle off the shelf, and another 25 years after that before self-serve liquor stores completely replaced the original counter service style. Strangely, the privately run Beer Store still sticks to the counter service method at most of their stores, but at least you don't need to fill out a form anymore.
In some parts of Toronto, prohibition lasted much longer, though. The neighbourhood now known as the Junction was still dry up until 1998, mostly thanks to the efforts of William Horace Temple (aka Temperance Bill) , a popular local politician and vocal opponent of the demon drink. It wasn't until 2001 that the first beer was poured at a bar in the area. High Park didn't vote to allow bars and liquor stores until 1997, and St Clair West was also alcohol free until 1994.