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Why Is Toronto Aesthetically/Architecturally Boring? Answer Needed!

Because there is no lifestyle at all.Developers only build bland box without style and beauty and bring no lifestyle with it.
We lack too a big strip mall like dix30 in Montreal or ICE district in Edmonton.

Ya, what Toronto really needs is a 800-car gravel parking lot.

Except that there is a history which partly explains Toronto's haphazard design and planning. Unlike New France, the colonial government at the time of Toronto's settlement, Britain, invested very little in its colonial possessions, though it took money out. That was what the American Revolution was about, the protection of property (liberty and the pursuit of happiness are built on this fundamental). That's why Toronto has been built by private capital, with few exceptions. The British Navy, Upper Canada Law Society, Landed Gentry, and United Empire Loyalists from the U.S. brought people, money, and institutions to Toronto. But make no mistake, Toronto is a business city, New York on a smaller scale. However, it is growing and deserves a higher level of attention to design, planning, and transportation.

Toronto is also a very young city compared to the likes of New York or Philadelphia.

How long has Toronto been Canada's biggest/most important city? Maybe 30 or 40 years?

As a side note, take a look at Quebec City. Most of the interesting buildings there were actually build by the British after they took over New France. These building were built to defend against an American invasion that never happened.
 
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Very true, there's some spectacular British architecture in Quebec, but I love Halifax and Nova Scotia for that. The Citadel and Privateers' Properties are pretty elegant, same with St. Paul's Church, which might as well be in Boston, because it was originally built in Boston (so was that church in Lunenburg, another awesome spot with a Common, just like Niagara On The Lake or Boston). Toronto has remnants of this in Old York and Corktown, also The Grange. Kingston probably has the best examples of this architecture in the province.
 

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