My honest answer: we don't really have any. There are lots of quaint, attractive, and pleasant small towns across the country, but they don't really offer a substantive, satisfying approximation of urbanity-in-miniature in the way that say, the Italian town above does.
It's just the way our towns are set up. There's usually a single, linear commercial corridor that gives the impression of urbanity, but it too quickly peters out into low-density, semi-rural residential at the margins to be conducive to a tangibly urban lifestyle. Like, this would be really impressive if it were one of several streets that looked the same:
https://goo.gl/maps/bbADQJNtooAy6HKT8. But turn any corner and it becomes this:
https://goo.gl/maps/dUMBgyZRkedh56Ha7. Nice, but not urban.
St. John's was mentioned above - I'd agree that that's probably about as small as you can go in Canada while still getting a real, comprehensive urban experience. You could maybe stretch it a little smaller to cities like Kingston, Trois-Riviers, or Saint John, but at even that point you're starting to have to make some concessions.