(Map of Barrie)

Barrie started as the end of a native trail from Kempenfelt Bay on Lake Simcoe to Willow Creek, a tributary of the Nottawasaga River. The trail thus connected Lake Simcoe to Lake Huron by way of the Nottawasaga River. During the War of 1812, the trail, now called the Nine-Mile Portage, became a strategic route for supplying the northern forts on the Upper Lakes, away from possible interference of American forces. In 1819, the military erected depots at the ends of the Portage, one at Fort Willow and the other on the shores of Kempenfelt Bay. The depots were for storing supplies for the new naval post at Penetanguishene. The Barrie depot was located at Memorial Square.

Within six years, the Portage was replaced as a supply route by the Penetanguishene Road and the extension of Yonge Street. The village of Kempenfelt at the southern end of the Penetanguishene Road became the settlement at this part of Lake Simcoe.

The town of Barrie was laid out in 1833 by William Hawkins, who also surveyed the Nine-Mile Portage for its improvement. At about the same time, Charles Rankin surveyed the Sunnidale Road from Barrie through Sunnidale Township. Barrie is named for a naval officer, Commodore Sir Robert Barrie, commander of the British naval forces at Kingston. The first settler in the area was Alexander Walker, who moved here to work on the improvement of the Portage and stayed. Soon he was joined by others. By 1837, more people lived at Barrie than at Kempenfelt. By 1847, the population had reached 500.

Of Barrie's early streets: Dunlop Street is named for Tiger Dunlop, army surgeon in the War of 1812, builder of the Penetanguishene Road, and founder of Goderich; Worsley Street is for Lieutenant Miller Worsley, commander of the Nancy; McDonald Street was originally McDouall Street named for Lt. Col. Robert McDouall, the commander of the expedition to supply Fort Michilimackinac in the War of 1812.