Noble beginnings

Dundas Street Beginnings, Part 1

On 23 September 1793, Mrs. John Graves Simcoe, wife of Upper Canada’s first Lieutenant Governor wrote in her often witty diary: “Captain Smith has gone to open a road to be called Dundas Street, from the head of the Lake to River La Tranche. He has 100 men with him… I hear that they kill rattlesnakes everyday, yet not a man has been bitten.” A month later, another entry again notes news about the beginnings of this famous old Ontario road, “Captain Smith is returned from cutting the road named Dundas. It is opened for 20 miles. They met with quantities of wild grapes, and put some of the juice in barrels, and Captain Smith told me it turned out very tolerable wine.”

So begins the history of Waterdown’s main thoroughfare, although work on the section through the village did not begin until two years later. While Lieutenant Simcoe is credited with the original idea of constructing a military highway across the Province of Upper Canada, the first proposal actually came from his father. Prior to his appointment by the British government, Simcoe had served in the American Revolutionary War, and while there, his father had collected old French maps. Among them, one showed a fur trading route from the vicinity of present day Dundas to London and the upper waters of the Thames River.

On his arrival in Upper Canada in 1792, Simcoe’s primary task was to initiate and supervise settlement. He was also given the responsibility of formulating plans to deal with the overwhelming fear of invasion from the recently liberated American colonies. His father presented him with the suggestion that a waterway dug along the fur trader’s route would provide an inland passage, well back from the border and relatively safe from a surprise attack.

After studying the suggestion and with the expectation of imminent border attacks, John Graves Simcoe and a military party travelled through the western part of the province, from Niagara to the border at Windsor during the winter of 1793. Guided by Indians and travelling by foot and sleigh wherever possible, Simcoe concluded that a road would be superior, since it would be multi-purpose, serving as a military link between Lakes Ontario, Erie, St. Clair and Huron, and as a spur to settlement.

Dundas looking west from First Street c.1905

Sylvia Wray is the former archivist with the Flamborough Archives. She can be reached through the Archives at

This article was originally published in the Flamborough Review, 14 October 2005.


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