In it’s earliest incarnation, Yonge St was a wild, tangled, muddy affair.

When soldiers from the Queens’ Rangers, a British Army regiment, finished clearing it at the shores of Lake Simcoe on Feb 16, 1796, it barely deserved the title of ‘street.’ At best, it was a rough track connecting the obscure army town of York (now Toronto) to the Upper Great Lakes.

Barely a decade had passed since the end of the American Revolution, and Lieutenant-Governor John Graves Simcoe feared that the Thirteen Colonies might add a 14th: Upper Canada. He commissioned Yonge St. in 1793 as a military highway for British troops in the event the U.S. invaded.

Simcoe named it after Britain’s then-Secretary of War—and Roman road expert—Sir George Yonge. But Yonge St. had little in common with the paved, rigorously marked, and ruthlessly straight roads of the Roman Empire. The Queens’ Rangers hacked Yonge St. out of the woods north of York, sometimes following the twists of Indigenous hunting trails. British settlers were required to keep roadside brush at bay. It was notoriously muddy in spring, prone to flooding, and unpaved.

Twenty years after the Queens’ Rangers cleared Yonge St., Simcoe’s fears of an invasion were realized. The U.S. Army crossed into Canada several times over the course of the War of 1812. Canadian militia companies and local farmers used Yonge to either get to (or avoid) battle. Ironically, Toronto’s first mayor, William Lyon Mackenzie, also used Yonge St to try and seize the Legislature of Upper Canada in 1837.

The street became more and more critical to Toronto as the 19th century rolled on. By the 1840s, horse-drawn omnibuses were hauling passengers from the St. Lawrence Market to the Red Lion Inn, north of Yonge and Bloor. In 1861, construction crews began laying down the city’s first streetcar tracks. The first subways rumbled under Yonge in 1954.

Two hundred years later, Yonge St. is still evolving.