I feel like the obvious answer to 'Most Canadian' is perhaps Winnipeg. Edmonton, Montreal, Ottawa, and Moncton are honourable mentions.
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Originally Posted by hipster duck
Even in the non-touristy parts, NF looks American. These kinds of wooden four square houses look like they belong in Buffalo.
This equivalent neighbourhood in nearby St Catharines is more Ontario-like, and could be in any Ontario city from Toronto to Orillia to Ottawa (differences in lot sizes, street widths and millions of dollars in property value notwithstanding).
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That's a good point. Also, on the touristy areas of Niagara, there's something to the specific aesthetic of Clifton Hill/Fallsview in the types of tourist traps, the chains, the garishness, the cheapness that make it feel like a very stereotypical hick American tourist trap town, like Branson, Missouri or Wall, South Dakota. The Hard Rock Cafes and TGI Fridays really seal the deal.
It has a very different feel/aesthetic than more typically Canadian-styled tourist traps, like Banff, Whistler, Magog, PEI, or even nearby in Ontario, places like Huntsville. More Beaver Tails and Moose Trinket Shops. Or, even closer to Niagara Falls, Niagara-on-the-Lake feels more typically Canadian.
I noticed it a lot between Alaska and the Yukon. The way towns like Ketchikan or Skagway cater to the boomer cruise ship crowd produces a different feel than Dawson City or Whitehorse or Carcross. Even the restaurant selection is entirely different (and much worse

).
Niagara Falls is a good contender for 'Least Canadian'. Windsor is another. I can see the argument for BC cities like Victoria, Vancouver, Kelowna, Abbotsford, but they don't feel exactly American (not that that is necessarily the criteria for being less Canadian looking).
I think the SW Ontario cities most directly influenced by the United States (Niagara Falls, Windsor, Sarnia) as well as British Columbian cities which are neither more Americanized nor distinctly Canadian in the same way as that which lies east of the BC-Alberta line are less Canadian seeming for different reasons.