23. Toronto, Canada
Aboriginal peoples have inhabited the area now known as Toronto for thousands of years. The city itself is situated on the southern terminus of an ancient Aboriginal trail leading north to Lake Simcoe, used by the Wyandot, Iroquois, and the Mississauga. Permanent European settlement began in the 1790s, after the broadly disputed Toronto Purchase of 1787, when the Mississaugas surrendered the area to the British Crown. The British established the town of York, and later designated it as the capital of Upper Canada. During the War of 1812, the town was the site of the Battle of York and suffered heavy damage by U.S. troops. York was renamed and incorporated as the city of Toronto in 1834, and became the capital of the province of Ontario during Canadian Confederation in 1867. The city proper has since expanded past its original borders through amalgamation with surrounding municipalities at various times in its history to its current area of 630.2 km2 (243.3 sq mi).