Colby Cosh on the origins of the name of Canada’s largest city (which, surprisingly, isn’t the Mississauga name for “big stink on the water”):
By the time of Franquelin, “Tkaronto” had already become “Taronto,” a generic name for the highway between Lake Simcoe and Lake Ontario. The Humber River was called the Toronto River by the French before Gen. John Graves Simcoe and the British got hold of everything. The word, in turn, became attached to a trading settlement at the southern end of the trail — a pretty crummy place, by all accounts, but one destined for bigger things as part of a global seafaring empire.
The miracle is that it held on to the name. Simcoe insisted that “Toronto,” on being anointed as the site of the new capital of Upper Canada in 1793, be dubbed “York” in honour of Prince Frederick (1763-1827), Duke of York and second son of George III. This Duke of York is the “Grand Old Duke of York” from the satirical verse about military futility. He was also commander-in-chief of the British armies that helped to chase Napoleon out of Europe twice, and is thought to deserve genuine credit for this, so be careful who you write insulting rhymes about.
Simcoe dubbed Toronto “York” just because he was sucking up to a very identifiable future boss, and for no other reason. The people of Toronto seem to have understood this and resented it. In the decades to come, it was occasionally observed that there were something like a dozen other places in Upper Canada called “York.” Moreover, Simcoe’s “Little York,” as it was often called, seems to have presented an increasingly embarrassing parallel with the Americans’ bustling New York.
In 1834, when the Legislative Council of Upper Canada decided that the capital needed to be formally incorporated as a city, the citizenry remembered that they belonged to “Toronto” and appealed to the council to have the more musical old name restored. Over four decades their annoyance had not receded. Diehards who wanted York to remain York for imperial-grandeur reasons were outvoted, and Toronto’s formal Act of Incorporation observes that “it is desirable, for avoiding inconvenience and confusion, to designate the Capital of the Province by a name which will better distinguish it.” The appellation “Toronto,” of course, had actually been nicked from a spot some way off, but the white settlers had mislaid that information, and didn’t check with anyone who would know better.