1780s: Jean Baptiste Rousseau straddles the many identities that are York. A first generation French Canadian trader, he works for the English and the Natives, and will help to repel American invaders. Rousseau is the first European resident of what will be York, the welcome wagon for the waves of refugees about to arrive from America.


When the French retreat from the region after their defeat on the Plains of Abraham in 1759, one of the few French left is Rousseau, a local fur trader. Son of a coureur de bois, he learns the languages of the Five Nations League and various Ojibwa dialects. He's an interpreter for the French traders, then the English, helping settle the Loyalists and negotiating land transactions with the Natives. He marries Margaret Clyne, the adopted white daughter of Chief Joseph Brant, solidifying his connections with the Native community. It is said that both he and Margaret court in the Mohawk language.

In 1791, Rousseau is running a small trading post on the shores of the Humber River, where Bloor West Village is today, when Upper Canada is created. He meets the first surveyors for the British Crown, who refer to him as Mr. St. Jean. Rousseau, or St. Jean as he is known locally, is much admired by the new Lieutenant Governor of Upper Canada, John Graves Simcoe who enlists him to negotiate with the Natives. Simcoe writes:

"He has all the requisites for that office and is equally agreeable to Brant and the Mohawks. As to the Mississaugas, (he is) the only person who possesses any degree of influence with those nations."

In 1793, Rousseau's daughter is the first European child born in York. But Rousseau has a hard time getting more land from the Crown, and moves south to Ancaster, near Hamilton where he runs a mill. He also converts to Anglicanism.

Rousseau leaves his mark all over Upper Canada. He's appointed to the militia as an ensign in 1797 and his name appears on the Second Toronto Purchase in 1805. As hostilities heat up between Canada and America, Rousseau is made a captain of the Indian Department in 1812. He reports to superiors about Native negotiations to keep the Six Nations neutral in the coming battle with the Americans.

On October 13, 1812, Rousseau fights at the famous battle of Queenston Heights, where Sir Isaac Brock is killed by American fire. A month later, he dies of pleurisy and is buried with full military honours in St. Mark's churchyard at Niagara.

1792: Lt. Governor John Graves Simcoe is a former British commander in the Revolutionary war. With the creation of Upper Canada in 1791, Toronto passes from native stewardship to British control. The new colony needs a government and safe capital. John Graves Simcoe arrives to oversee both.


Simcoe sails into Toronto harbour in 1792 with his wife and family aboard the 120-tonne schooner "The Mississauga".. Within a month of establishing a military post, his Queen's Rangers fire a 21-gun salute along the shore, inaugurating the site for a new town. Simcoe calls it York, in honour of King George's son, the Duke of York - the same one the children sing about.

"The Grand old Duke of York
He had ten thousand men
He marched them up to the top of the hill
And he marched them down again."

Simcoe chooses Toronto because he recognizes the strategic value of its natural harbour against Americans attack. Just as importantly, York is a lot further from the border than the temporary capital of Newark (now Niagara-on-the-Lake).

As a soldier in the Revolutionary War, Simcoe harbours an abiding hatred of the Americans; especially their tradition of slavery. In his first session of Parliament, he proposes legislation to abolish slavery in Upper Canada. It's the first distinctly human rights statute against slavery in the entire British Empire. Simcoe writes that he cannot assent to any law which: "discriminates by dishonest policy between the natives of Africa, America or Europe."

Though he stays only four years, Simcoe lays the foundations for Toronto, establishing a judiciary, a cleared town site, roads; and creating a land grant system that lures Loyalists to the village. It is his need for settlers, his tolerance for immigrants that shapes Upper Canada for the next several generations. His suspicion of the French is another lasting legacy that will colour the psyche of Toronto.


1792: Mrs. Elizabeth Posthuma Simcoe, the adventurous wife of Lieutenant Governor John Graves Simcoe, arrives in Toronto in 1792 with a boatload of ball gowns, jewelry, and sterling silver. She's accompanied by a French chef and 3 of her youngest children. For the next four years her home will be an elaborate 30 foot, embroidered canvas tent erected on a platform along the lakeshore. The wealthy, petite Englishwoman is curious, free-spirited person, open to the adventures awaiting her in Upper Canada. She loves the frontier and the danger it offers. Mrs. Simcoe rides horses through the forests, paints landscape watercolours and shows an interest in local Natives. She also keeps a diary, offering modern readers a lasting impression of 18th century Toronto.

"At eight this dark evening we went to see salmon speared - large torches of white bark being carried in the boat, the blaze of light attracts the fish, which the Indians are dexterous at spearing. The manner of destroying the fish is disagreeable, but seeing them swimming in shoals around the boat is a very pretty sight."

Mrs. Simcoe earns a reputation for strong passions and unusual proclivities. According to her diaries, she likes setting fires in nearby pastures, excited by the flames burning the grasses. Historian Marion Fowler thinks there's more to it. According to Ms. Fowler, the fires are burned only when Mrs. Simcoe is in the steamy company of one of the Governor's men, the young and handsome Colonel John Talbot.

William Moll Berczy is remembered as one of Canada's first portrait painters, but the German immigrant is a highly trained engineer with architectural skills. He designs St. James, the first Anglican Church 1806, as well as the first bridge on the Don River.


Leading 600 countrymen north from America in the l790s, Berczy makes a deal with Simcoe to bring in settlers and to build roads in exchange for free land to farm. During their early years clearing mosquito-infested bush, many of the Germans die from Malaria. Road building falls behind. Nervous that this German community may not be loyal to the Crown, the land grants are not honoured by Simcoe's successors. Berczy's original farm and the descendants of these first settlers, still remain in the Markham area.