On Sept. 25, 1793, John Graves Simcoe, the first lieutenant-governor of Upper Canada, left York at the head of a small expedition. At a time when Simcoe was primarily concerned with building new roads and military posts to defend the young province from the United States, the goal of the expedition was to find a good location for a military harbour on Georgian Bay and a good route for a road connecting that harbour to York. The expedition would take Simcoe and his men throughout much of what is now Simcoe County, give the modern names to parts of our county’s most prominent lake and set in motion the early settlement of the area.

On his journey, the 41-year-old Simcoe was accompanied by Captain Henry Darling, Home District sheriff Alexander Macdonnell, land surveyor Alexander Aitken and twelve soldiers of the Queen’s Rangers led by Lieutenant James Givins, as well as Jack Sharp, the governor’s large Newfoundland dog. At the time of their departure, York was just a compact, recently surveyed ten-block townsite near where the Don River emptied into Toronto Bay. Planning to use the new town as the temporary capital of the province until his desired location at London could be established, for the past several months, Simcoe had been living there with his family in a canvas tent inherited from British explorer Captain James Cook.

Led by several First Nations guides, the expedition travelled by horseback along the Toronto Carrying Place, a traditional First Nations trail that connected Lake Ontario with what is now Lake Simcoe. Departing from the mouth of the Humber, they followed the trail far up the river, then east onto the Oak Ridges Moraine and north along the Holland River from its headwaters. On Sept. 29, the expedition arrived at the marshy delta where the Holland River emptied into the southernmost bay of a lake French fur traders had named Lac aux Claies. Simcoe renamed the lake Simcoe, after his late father, Captain John Simcoe of the Royal Navy. Cook’s Bay was named after the famous Captain Cook, who had served under his father in the 1750s.

From there, the expedition boarded canoes and set out across the northern side of Lake Simcoe, passing the mouth of the lake’s westernmost bay, which Simcoe named Kempenfeldt Bay after his father’s friend Rear Admiral Richard Kempenfeldt. At the northern end of the lake, the expedition portaged around the ancient First Nations fishing weirs that had inspired the lake’s former French name, Lake of Trellises, and set out across Lake Couchiching, then up the Severn River and into Georgian Bay. Over the next few days, Simcoe carefully examined several bays along the south shore of Georgian Bay and identified a few potential harbours, particularly at what is now Penetanguishene.

However, by the time they were ready to return, the expedition had become lost. Fortunately, Simcoe, a veteran of many forest expeditions during the American Revolution, was able to use his compass to reorient his men and the expedition headed home the way they had come. Along the way, they stopped at an Ojibway village whose chief, Canise (Great Sail), the son of a recently-deceased friend of the lieutenant-governor, gave Simcoe a beaver blanket and directions for a more direct route home to York from the mouth of the Holland River. During the second week of October, the expedition followed Canise’s route south from Lake Simcoe along the Holland River, then overland. By Oct. 13, the party had reached the eastern branch of the Don.

By this point, the expedition was running so short of provisions, they were beginning to contemplate eating the governor’s dog. Fortunately for Jack Sharp, on Oct. 14, with only one day’s worth of provisions left, the party crossed the 4th Concession Line of York Township, the first road they had seen in almost three weeks. By 3 p.m. that afternoon, Simcoe and his men had arrived back at York.

Simcoe’s expedition had several important consequences for the history of our county. It gave the modern names to Lake Simcoe and its two largest bays. It also identified the route for what became Yonge Street, which was eventually constructed along the route pointed out to Simcoe by Canise and, once completed, enabled the flow of settlers into much of Simcoe County. The expedition also identified Penetanguishene’s potential as a military harbour on Georgian Bay and, once a permanent military post was established there in 1818, it drew some of the earliest settlers to Simcoe County. For the history of Simcoe County, it was not an inconsequential journey.