Here are some starters from Quebec...
I agree that Canada punches way below its weight on that matter, but I also think that people may only not know those towns well enough. For example, Québec, Ontario and New Brunswick (the provinces I am the most familiar with) have hundreds of interesting little villages and towns...
Also, we must not forget that we are the "new world" compared to Europe. That means that the early settlers in North America tried to develop new forms of urbanity.
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Baie-Saint-Paul, QC (pop. 7 378), for its natural setting and its main streets, cafés, and culture
Baie Saint-Paul, Québec by
Oddition, on Flickr
Baie St Paul - Québec by
Vince Arno, on Flickr
DSC_7283_7307 by
Sébastien Girard, on Panoramio
Trois-Pistoles, QC (pop. 4 590), for its region and history
Trois-Pistoles-1.jpg by
nicogag, on Flickr
Montmagny, QC (pop. 11 525)
Source :
Google Street View
Source :
Panoramio
Montmagny, Québec by
piermd, on Flickr
La Prairie, QC (pop. 24 162), for its proximity to Montreal and its nice almost pedestrian downtown
Source :
Google Street View
Source :
Panoramio
Source :
Panoramio
Source :
Panoramio