^There's one older car in the photo but, yeah, I'm with you.
Other clues:
Suits and fedoras could place it at any point after 1930 (I'm guessing);
Neon signage, again, probably after 1930, more likely the 40s;
Parking meters, apparently, first came into use in Canada in the early-40s.
Yeah, it seems possible this is the early-50s. However, I don't see any evidence of those big, beautiful 50s cars, so I'm going to put money on it being the late-40s.
Fun game! Great idea for a new thread! Guess the date of the photo...