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In 1787, the British Lord Dorchester arranged for the Toronto Purchase with the Mississaugas of the New Credit First Nation, thereby securing more than a quarter of a million acres (1000 km In 1793, Governor John Graves Simcoe established the town of York on the Toronto Purchase lands, instead naming it after Prince Frederick, Duke of York and Albany.

Simcoe decided to move the Upper Canada capital from Newark (Niagara-on-the-Lake) to York, The York garrison was constructed at the entrance of the town's natural harbour, sheltered by a long sandbar peninsula.

Because of its provincial capital status, the city was also the location of Government House, the residence of the viceregal representative of the Crown in right of Ontario.

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American soldiers destroyed much of the garrison and set fire to the parliament buildings during their five-day occupation.

The sacking of York was a primary motivation for the Burning of Washington by British troops later in the war.

This refers to the northern end of what is now Lake Simcoe, where the Huron had planted tree saplings to corral fish.

However, the word "Toronto", meaning "plenty" also appears in a French lexicon of the Huron language in 1632, A portage route from Lake Ontario to Lake Huron running through this point, the Toronto Carrying-Place Trail, led to widespread use of the name.

With 2,731,571 residents in 2016, it is the largest city in Canada and fourth-largest city in North America by population.