The route for the road was surveyed in 1808 by Samuel Wilmot. After the British captured Fort Michilimackinac in the War of 1812, the requirement to supply the captured fort created a need for ships to be built on Lake Huron, which in turn meant that an effective supply route needed to be cut. The decision was made to cut the road in November 1814 by General Gordon Drummond. It was completed by the following spring. Following the war, the surrounding land was purchased in the Lake Simcoe–Lake Huron Purchase from the Chippeway First Nation and the road opened for settlement. It was treated specially by the crown land office in that the strategic value of the route to the naval base led to the road being preferred for military settlers. Large numbers of soldiers who had served in Canada or elsewhere throughout the British Empire were settled along the road and in the vicinity of Penetanguishene, as well as pensioners from Chelsea Hospital. Many of the commuted pensioners were reduced to a state of extreme poverty.