In 1937 Ontario passed a law that required bars to have separate entrances and drinking areas for men and women - one source quotes a now removed article from a BC paper which said this seems to have been part of an anti-VD campaign in Canada. There had to be some kind of barrier between the side in the bar where women sat and where men sat, but it was "Ladies and their (male) Escorts" on the women's side and no women on the men's side. To this day many old bars in Ontario still have two doors, although the separation barriers are long gone.
This was in effect up at least into the 1970s, and in Quebec many taverns were off limits to women in practise until the 1980s - in 2007 a woman was refused service at a gay bar in Montreal.
This is a building on Beckworth and William streets, in Smith Falls, Ontario in 2008 that probably was a hotel with a bar - sign is now gone.