Today in 1795, John Graves Simcoe, as the Lieutenant Governor of Upper Canada, established York (modern Toronto) and began building Yonge Street, the “longest street in the world” until 1999. Now WE know em


John Graves Simcoe was born February 25, 1752 in Cotterstock, England.

His father was a captain in the Royal Navy and commanded the HMS Pembroke with James Cook as his sailing master during the 1758 siege of Louisbourg.

His godfather was British admiral Samuel Graves.

John was the only child of four to survive past childhood.

When his father died of pneumonia in 1759, John and his mother moved to her paternal home in Exeter.

John went on to attend Eton College and began studies at Oxford University for a year before deciding to follow in his father’s footsteps and join the military.

Then in 1770, as an ensign with the 35th Regiment of Foot, John was dispatched to the American Thirteen Colonies.

During the Revolutionary War at the Siege of Boston, John purchased a captaincy in the grenadier company of the 40th Regiment of Foot.

With the 40th, John saw action in New York and New Jersey before being wounded at the Battle of Brandywine on September 11, 1777.

On October 15, 1777, John was offered the command of the Queen’s Rangers (a well-trained light infantry unit).

His unit saw extensive action during the Philadelphia campaign, including a successful surprise attack he planned and executed at the Battle of Crooked Billet on May 1, 1778.

Later in 1778, John and his Rangers attacked Judge William Hancock’s house, killing 10 American rebels as well as Judge Hancock.

Then during the winger of 1779, John and his Rangers attempted unsuccessfully to capture George Washington himself before John Simcoe was captured.

He was eventually released in 1781 and rejoined his unit in Virginia before the Siege of Yorktown.

A few months later, John returned to England as a Lieutenant-Colonel.

In 1787, John published a book on his experiences with the Rangers, titled A Journal of the Operations of the Queen’s Rangers from the end of the year 1777 to the conclusion of the late American War.

He married Elizabeth Gwillim in 1782 and went on to have five children before being posted as the first Lieutenant Governor of Upper Canada in 1791.

Lieutenant Governor of Upper Canada

The Province of Upper Canada was created under the Constitutional Act of 1791, a few years after the end of the American Revolutionary War.

The area had been newly settled mostly by Anglo-American and other Loyalists from the Thirteen Colonies, as well as the Six Nations of the Iroquois, who had been allies during the war.

The Crown had purchased land from the Mississaugas and other First Nations in order to give Loyalists land grants in partial compensation for property lost in the United States, and to help them set up new communities.

When John Simcoe was appointed lieutenant governor and made plans to move to Upper Canada with his wife Elizabeth, daughter Sophia, and newborn son Francis. John decided to leave his other three daughters behind with their aunt.

The Simcoe family left England in September and arrived on November 11, 1791.

As this was too late in the year to make the trip to Upper Canada because of severe weather, the Simcoes spent the winter in Quebec City.

The next spring John moved his family to Kingston and then Newark (now Niagara-on-the-Lake).

The Constitutional Act of 1791 stipulated that the provincial government would consist of the Lieutenant-Governor, an appointed Executive Council and Legislative Council, and an elected Legislative Assembly.

The first meeting of the nine-member Legislative Council and sixteen-member Legislative Assembly took place at Newark on September 17, 1792.

John’s first priority was dealing with the effects of the Northwest Indian War, in which American Indians warred with the United States over encroachment in their territory west of the Appalachian Mountains.

Then war broke out between Britain and France in 1793.

Although the United States pledged neutrality, its sympathies were with France, an ally during the Revolution.

John Simcoe was instructed to avoid giving the U.S. reason to mistrust Britain but, at the same time, to keep the Native Americans on both sides of the border friendly to Britain.

He became concerned about the possibility of the United States entering British North America in support of their French allies.

In particular, the location of Newark (now Niagara-on-the-Lake), the first and former capital of Upper Canada, was in danger of being attacked by the Americans from the nearby border. Additionally, US forces could easily sever British access to the upper lakes at Lake St. Clair or the Detroit River, cutting the colony off from the important trading post at Michilimackinac.

John planned to move the capital to a better-protected location and build overland routes to the upper lakes as soon as possible.

He thus established York, as Toronto was originally called, with its naturally enclosed harbour, as a defensible site for a new capital.

To provide communications between the site and the upper lakes, he planned two connected roads, the first running north from York to Lake aux Claies, the second joining Lake aux Claies with Georgian Bay.

This would allow overland transport to the upper lakes, bypassing U.S. strongholds.

John decided to name this road “Yonge” after his friend and Minister of War Sir George Yonge, an expert on ancient Roman roads.

The route from Lake Ontario to Lake aux Claies is still known today as Yonge Street, and the second leg to Georgian Bay was long known as the Penetanguishene Road.

Before the construction of Yonge Street, a portage route, the Toronto Carrying-Place Trail, had already linked Lake Ontario with Lake aux Claies.

Then on September 25, 1793, John Simcoe and a small party of soldiers and native guides started northward along the trail, establishing the Pine Fort on the western branch of the Holland River, near the modern location of Bradford.

Stopping only to rename Lake aux Claies “Simcoe” in memory of his father, the party continued north to Lake Couchiching, and then down the Severn River to Georgian Bay.

Here John selected the site of Penetanguishene as the location for a new naval base and port.

On his return, John met with an Ojibway named ‘Old Sail’ and was shown a new route along another arm of the trail, this one starting on the eastern branch of the Holland River and thereby avoiding the marshes of the western branch (today’s Holland Marsh).

They left Pine Fort on October 11 and reached York on the 15th.

John selected this eastern route for his new road, moving the southern end from the Rouge River to the western outskirts of the settled area in York, and the northern end to a proposed new town on the Holland River, St. Albans.

This road was officially called ‘Concession 1’ at first with Concessions 2 etc. on either side.

Construction of Yonge Street

The following spring, John Simcoe instructed Deputy Surveyor General Augustus Jones to blaze a small trail marking the route.

John initiated construction of the road by granting land to settlers, who in exchange were required to clear 33 feet of frontage on the road passing their lot.

In the summer of 1794, William Berczy was the first to take up the offer, leading a group of 64 families north-east of Toronto to found the town of German Mills, in modern Markham.

By the end of 1794, Berczy’s settlers had cleared the route around Thornhill.

However, the settlement was hit by a series of setbacks and road construction stalled.

Then on December 28, 1795, work on Yonge Street started again when John had the Queen’s Rangers take over the project.

They began their work at Eglinton Avenue and proceeded north, reaching the site of St. Albans on February 16, 1796.

The road was extended south from Eglinton to Bloor Street later in 1796.

In July of 1796, poor health forced John Simcoe to return to England.

He was unable to return to Upper Canada and resigned his office in 1798.

In 1812 the route was extended from Queen Street to the harbour.

The southern end of the road was in use in the first decade of the 19th century, and became passable all the way to the northern end in 1816.

By 1828 the entire southern portion had been solidified with gravel.

St. Albans never developed as John Simcoe had hoped, but the town of Holland Landing eventually grew up on the site, a somewhat more descriptive name. Holland Landing was settled by Quakers who moved into the area after having left the United States in the aftermath of the American Revolution. The settlers were branching out from their initial town of “Upper Yonge Street”, which later became Newmarket.

John Graves Simcoe died October 26, 1806 October 26, 1806 at Exeter, England at the age of 54.

Then his Yonge Street came close to its original military purpose during the War of 1812, when construction of a new fleet of first-rate ships began on the Lakes, necessitating the shipment of a large anchor from England for use on a frigate under construction on Lake Huron.

The war ended while the anchor was still being moved, and now lies just outside Holland Landing in a park named in its honour.


The 1903 unveiling of the General John Graves Simcoe monument at Queen's Park in Toronto.

The 1903 unveiling of the General John Graves Simcoe monument at Queen’s Park in Toronto.

Yonge Street as the “longest street in the world”

Yonge Street was formerly a part of Highway 11, which led to claims that Yonge Street was the longest street in the world.

Running from the shores of Lake Ontario, through central and northern Ontario to the Ontario-Minnesota border at Rainy River, together they were over 1,896 kilometres (1,178 mi) long.

The Guinness Book of World Records recognized Yonge Street as the longest street in the world as late as 1999.

Changes in provincial responsibility separated the now locally-funded and controlled Yonge Street from Highway 11 during the 1990s.

As a result, Highway 11 does not start until Crown Hill just outside of Barrie, several kilometres north of where the name “Yonge Street” ends. The Guinness Book of World Records no longer lists Yonge Street as the longest street in the world, citing instead the Pan-American Highway as the world’s longest “motorable road”.

Now WE know em




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