The Origins of Yonge Street

Many people know that Yonge Street is one of the longest streets in the province, stretching all the way up from Toronto Waterfront to Barrie. But did you know it also dates to before Confederation occurred in Canada? In this post, we will explore the origins of Yonge Street and the way in which it contributed to the growth of Holland Landing.

The place where Yonge Street now stands today has been well travelled. Prior to colonial settlement, it was part of the way that First Nation bands would get from Lake Ontario up to Lake Simcoe, using a combination of portages and water routes. Simcoe first visited this area in 1793, when he journeyed from York to Matchedash Bay. On Friday, September 25, his wife Elizabeth Simcoe recorded in her diary that “Governor [Simcoe] went to see a very respectable Indian named “Old Sail”, on a branch of Holland’s River. He advised him to return by the eastern branch of it to avoid the swamp” (Diary of Mrs. Simcoe, 1911, 196).

Figure 1: Portrait of Sir John Graves Simcoe, Lieutenant of Upper Canada, 1791 - 1796.

Given the long distances that separated military bases throughout Upper Canada by canoe and on foot, Simcoe decided that the area needed a more formal military-style road, connecting the burgeoning community of York (now called Toronto) to Lake Simcoe. The route from Lake Simcoe would also lead into Matchedash Bay, close to where the established military outpost was located at Penetanguishene. Simcoe named the new road Yonge Street, after his friend Sir George Yonge, who was an expert on ancient Roman roads. Deputy Surveyor General Augustus Jones was chosen to go out and blaze a trail for the new road, undertaking his survey of the road in the winter of 1794 and completing it up to Lot 111 in East Gwillimbury.

Simcoe then began offering land grants to settlers, stating that one of the requirements upon the land being granted to them was the need to clear 33 feet of frontage on the road passing their lot. A Dutch settler named William Berczy managed to procure enough land so that 64 families could settle in the north-east part of Toronto, and founded the town of German Mills, which is now known as Markham. However, after about a year, the settlers had only cleared the road as far as modern-day Thornhill, and road construction had stalled amid a series of setbacks.

Figure 2: An imagined scene showing the Queen's Rangers cutting down trees and clearing brush for Yonge Street. Line drawing by Charles William Jefferys.

As a result, Simcoe had to send in the Queen’s Rangers to restart work on the road in 1795. They managed to reach the townsite of St. Albans (now Holland Landing) on February 16, 1796. When settlement was opened in East Gwillimbury in 1800, one of the conditions for farmers along that route was that they needed to spend 12 days a year clearing the road of debris and fallen logs.

If you want to learn more about this fascinating topic, check out F.R. Bercham’s “The Yonge Street Story: 1793 - 1860” and “Opportunity Road: Yonge Street 1860 – 1939” at your closest local library.