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| 1791 | Upper Canada becomes a separate British colony with John Graves Simcoe as lieutenant governor. |
| 1793 | Simcoe moves to Toronto with his wife, Elizabeth. Watercolours of York by Elizabeth Simcoe . Deputy-surveyor Alexander Aitken lays out a 10-block town and township lots north of the base line (Queen Street). This is Toronto's first official plan. Plan of York Harbour, 1793 |
| 1796 | Yonge Street is completed to Holland Landing. Settlers Duties on Yonge Street, 1798 The first Parliament buildings are constructed at the foot of Parliament Street. |
| 1799 | Work starts on Danforth Road connecting York to the eastern part of the province. |
| 1801 | Eighteen blacks - free and slaves - are among York's 681 residents. A List of the Inhabitants in the Townships of York, Scarborough, & Etobeconk, in the Year 1801 |
| 1812 | War of 1812 begins. United States declares war on Great Britain and strikes at Canada, Britain's only possession in North America. Brock Proclamation, 1812 |
| 1813 | Constrction of a 30-gun warship at York attracts the Americans to attack. Sir Isaac Brock, under construction at York, April 1813 Fourteen American ships and 1,700 troops capture York on April 27. Arrival of American Fleet Victory by Gen. Dearborn, May 1, 1813 Prominent York citizens negotiate the surrender. Terms of Capitulation, first draft American battle accounts and final terms of Capitulation John Strachan's version of events, May 8, 1813 |
| 1817 | John Ridout is killed in a duel with Samuel Peters Jarvis near the corner of present-day Bay and Wellesley streets. |
| 1825 | Bank of Upper Canada opens on the northwest corner of Duke and George streets. |
| 1827 | King's College receives a royal charter. |
| 1832 | Cholera kills 237 people in York, and more than 500 in 1834. Transcript: Letter from cholera victim, 1834 |
| 1834 | The Town of York becomes the city of Toronto. York Commercial Directory 1833-4 William Lyon Mackenzie is made mayor. Election Notice, 1834 |
| 1836 | Provincial elections are held: Lieutenant-Governor Sir Francis Bond Head campaigns against the Reformers. Farmers! Beware!, 1836 |
| 1837 | Rebellion of 1837. Mackenzie leads an unsuccessful rebellion against the ruling class, the "Family Compact." History of the Battle of Toronto |
| 1838 | The rebellion is crushed. Rebels Samuel Lount and Peter Matthews are hanged for treason. Prisoner's box, 1838 |
| 1839 | Regatta held on Toronto Bay. |