According to Henry Scadding in Toronto of Old, on Thursday, May 9th, 1793, the Niagara-based Upper Canada Gazette reported the following:

On Thursday last his Excellency the Lieutenant-Governor, accompanied by several military gentlemen, set out in boats for Toronto, round the Head of the Lake Ontario, by Burlington Bay; and in the evening his Majesty’s vessels the Caldwell, and Buffalo, sailed for the same place.

The Lieutenant-Governor of Upper Canada, John Graves Simcoe, had left for Toronto on May 2nd, and would return to Niagara on the 13th, as reported in the May 16th Gazette.

An earlier letter, dated April 5th, 1793, from Simcoe to the Lieutenant-Governor of Lower Quebec, Major-General Clarke, suggests that Simcoe’s May visit to Toronto was his first.

In her diary, on Monday, July 29th, 1793, Elizabeth Simcoe described leaving Niagara and arriving at Toronto for the first time.  There is no town in July of 1793.  Toronto is a bay covered in forest.  Her husband has had a soldiers’ camp set up at the site of present-day Fort York. 

“Mon. 29th – We were prepared to sail for Toronto this morning, but the wind changed suddenly.  We dined with the Chief Justice, and were recalled from a walk at nine o’clock this evening, as the wind had become fair.  We embarked on board the “Mississaga,” the band playing in the ship.  It was dark, so I went to bed and slept until eight o’clock the next morning, when I found myself in the harbour of Toronto.  We had gone under an easy sail all night, for as no person on board had ever been at Toronto, Mr. Bouchette was afraid to enter the harbour till daylight, when St. John Rousseau, an Indian trader who lives near, came in a boat to pilot us.”

Library and Archives Canada, no. 1972-118-2

Elizabeth Simcoe was born Elizabeth Posthuma Gwillim in England. The exact date and place of birth are uncertain, as she was orphaned as a baby and lived with her uncle, Admiral Graves, and her aunt Margaret. She married her uncle’s godson, John Graves Simcoe, when she was sixteen.

In 1791, her husband was appointed the first lieutenant-governor of Upper Canada, and they made the trip from England. After spending some time in Quebec and then Newark (now Niagara-on-the-Lake), she arrived at York on July 30th, 1793. In 1796, her husband was given a leave of absence and the Simcoes left for England, never to return.

During her time in Canada, she kept a diary and produced many sketches and watercolour paintings of her surroundings.

Credit: Exclusive permission to reproduce this image was very kindly provided to the Toronto Project by the Map and Data Library, University of Toronto. This image may not be reproduced. Original link found here.
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In 1788, Alexander Aitken (sometimes spelled Aitkin), a deputy surveyor, had prepared an initial survey of York Harbour on the instructions of the Governor-in-Chief, Lord Dorchester (Sir Guy Carleton, First Baron Dorchester). In 1793, he was asked by the Lieutenant-Governor of Upper Canada, John Graves Simcoe, to prepare a new survey, which included the proposed location of a blockhouse to command the entrance of the harbour, as well as a battery and barracks for the Queen’s Rangers. The soundings for this survey were taken by Joseph Bouchette.

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Description: Watercolour painting of Harbour in 1793, looking west to the Queen’s Rangers camp, which would eventually develop into Fort York, located at what is now approximately the foot of Bathurst Street).
Date: 30 July, 1793
Author: Elizabeth Simcoe

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Description: Watercolour painting of Harbour in 1793 (or approximately), looking west from the mouth of the Don River.
Date: circa 1793
Author: Elizabeth Simcoe