Originally Posted by rousseau
My understanding is that aside from the obvious choices of Toronto and Montreal, the only places in Canada that do literally have thirty to forty distinctive neighbourhoods within them that you couldn't ever mistake one for the other, the rest of the larger cities in Canada don't generally have more than several distinctive neighbourhoods forming a small portion of otherwise generally generic urbanity.
My only prairie experience is with Winnipeg, but it's a good example. You've got the rougher North End, the granola-ish Wolseley, francophone St. Boniface, posh Wellington Crescent, ostensibly hipster Osborne Village and ostensibly Little Italy-ish Corydon, but the rest of the city is essentially indistinguishable for all intents and purposes. So is Winnipeg a "great neighbourhood city"?
Of course not. It's a nice place and all, but no metro of 700,000 people in North America is going to provide distinctive, tradition-rich neighbourhoods that you could spend time exploring. It's just not in the cards.
This seems like an odd way to frame the discussion. What are the bigger cities in Canada, aside from Toronto and Montreal? Vancouver was a pioneer town in 1880. If you expand your horizons to include the rest of North America, there are many cities of any size that have a great wealth of impressive neighbourhoods that stand up to Montreal or Toronto. And the historic parts can be a much higher proportion of the town (25-90%) than what you see in Montreal or Toronto.
I don't know Winnipeg well enough to comment but in Quebec City or Halifax, the old parts are extensive and will take you days to cover on foot (I know this because every time I visit I run out of time). They're not one or two little clumps of quirky shops in brick buildings from the early 1900's surrounded by suburbia, and they both offer different things from Montreal or Toronto.
The US has lots of great old cities like Portland ME, Boston, NYC, Philadelphia, Baltimore, Charleston, New Orleans, and on and on. A lot of the US cities make their Canadian equivalents look shabby. Mexico and the Caribbean can knock the socks off of Canada and the US for historic architecture and, often, vibrancy. Some of those cities are huge but others are not, e.g. San Francisco de Campeche has thousands of historic buildings, is a UNESCO heritage site, and has around 200,000 people.
The notion that you can't have an interesting city without millions of people is not true when you expand your horizons beyond Ontario and Western Canada. And even in those places it's a simple consequence of the fact that cities in those places are so suburban.