Within the community of Waverley, the route encounters the northern terminus of former Highway 27, now Simcoe County Road 27.

It curves around the western side of a large hill before entering the community of Wyebridge, where it crosses the Wye River.

The Penetanguishene Military Post was started before the war, however, lacking a suitable overland transport route, passage from York to Lake Huron continued via the Nottawasaga.

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.

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.

[7][8] In 1824, construction began to extend Penetanguishene Road south (with a U-shaped course around Kempenfelt Bay) to with connect with Yonge Street at Holland Landing.

[16] As part of a series of budget cuts initiated by premier Mike Harris under his Common Sense Revolution platform in 1995, numerous highways deemed to no longer be of significance to the provincial network were decommissioned and responsibility for the routes transferred to a lower level of government, a process referred to as downloading.

The 7.3-kilometre (4.5 mi) section north of Highway 12 into Penetanguishene primarily served local traffic and was downloaded on the same day.

Burke was born in Barrie and grew up in Midland; the freestyle skier died in a training accident in January 2012.