North America's First Valentine — When The Founder Of Toronto Fell In Love With A Rebel Spy

1779. The American Revolution was at its bloody height. John Graves Simcoe had already seen plenty of action. Years before he founded the city of Toronto, Simcoe was a young officer in the British army, fighting against the American rebels. And there, in the middle of that brutal war, he was about to fall in love.

That winter, Simcoe found himself living just outside New York City. The area was controlled by the British at the time, but there were still plenty of American rebels around. So Simcoe spent his days on patrol with his men, searching for revolutionaries, fighting terrible, bloody battles. Over the course of the war, he would gain a reputation as a hero on the British side — leading his Queen's Rangers on guerrilla-style raids, their green uniforms blending in with the forests, a white crescent moon on their hats in honour of Diana, Goddess of the Hunt. Many of the American rebels, on the other hand, would come to see him as a particularly vicious foe, accused of massacres and remembered more than 200 years later as a psychopathic villain in an ahistorical Netflix show.

But at night, things were much more peaceful. Simcoe was billeted with an American family who lived in Oyster Bay, a small community on Long Island. The Townsends were slave-owning tobacco farmers: they enslaved eight people at their home and even more on their plantation. Simcoe would later earn a complicated reputation as a passionate abolitionist, but even so, he seems to have enjoyed his time living with the Townsends. In fact, it was there during those long winter nights on Long Island that he was destined to fall in love.

Sarah Townsend was 18 years old; the middle of the three Townsend girls. Sally to her friends. Simcoe was 27, but still a dashing young officer looking for a wife. They say his fellow soldiers were deeply jealous of the time he got to spend with Sally. "She was the toast of these young men," one account would later remember, "and Simcoe was regarded as a most fortunate being in basking in the daily sunshine of her charms." The two are said to have spent plenty of time flirting that winter, and by the time February 14th came around, the young Townsend had captured Simcoe's heart.

To prove the depth of his feelings, the young man turned to a relatively new English tradition. People had been sending Valentine's Day cards for centuries, but it was over the course of the 1700s that they really evolved into the popular romantic tradition we know today. And Simcoe seems to have fully embraced it — seeing it as a chance to show off his writing skills. He'd studied poetry at school and thoroughly enjoyed writing his own verse. So, to celebrate St. Valentine's Day in 1779, Simcoe penned an ode to Sally Townsend — and then gave it to her.

The poem is a fairly epic one by the standards of a Valentine — it’s thirteen stanzas long and more than 300 words — but it begins like this:

Fairest Maid where all is fair
Beauty’s pride and Nature’s care;
To you my heart I must resign
O choose me for your Valentine!

Later, it gets a bit more wordy:

Thou knows’t what powerful magick lies
Within the round of Sarah’s eyes,
Or darted thence like lightning fires,
And Heaven’s own joys around inspires;
 

And finally, it transforms into a prayer to the God of Love — a plea that there will be more to Simcoe's life than just endless war:

[God] bad'st me change the pastoral scene,
Forget my Crook; with haughty mien
To raise the iron Spear of War,
Victim of Grief and deep Despair:
Say, must I all my joys forego
And still maintain this outward show?
Say, shall this breast that's pained to feel
Be ever clad in horrid steel?
Nor swell to other joys than those
Of conquest o'er unworthy foes?
Shall no fair maid with equal fire
Awake the flames of soft desire[?]
[…]
"Fond Youth," the God of Love replies,
"Your answer take from Sarah's eyes."

But that wasn't all. Simcoe had more to offer than just his poetry. He also attached a sketch: two hearts, inscribed with both of their initials and joined together by Cupid's arrow.

Today, it's considered to be the very first Valentine in the history of North America.

You might be wondering how young Sally Townsend could resist such an historic overture. But the truth is that it didn't matter how much Simcoe felt for Townsend, how flattering his poetry, or romantic his art. The two could never be together. The founder of Toronto had fallen in love with the wrong woman. You see, Sally Townsend was a rebel spy.

Now that the British were in control of New York, the American general George Washington was desperate for information from inside the occupied city. So, he established a spy ring to feed him secrets from New York, as well as from Long Island and Connecticut. He called it The Culper Ring. Sally’s brother Robert was one of three men enlisted to run the scheme — and while the details are far from clear, many historians believe that he brought his sister on board as an informant.

The Culper Ring proved to be a huge success. It was in operation for five years and tipped Washington off to surprise attacks, a British counterfeiting scheme, and maybe even a plot on the general’s own life. It’s been called “the spy ring that saved America.”

But with his head firmly over his heels, Simcoe had no clue the young woman he’d fallen in love with was actually a secret rebel. Some historians suggest that while he was busy wooing the lovely young Townsend, she may have been spying on him the whole time.

One story in particular raises eyebrows. The British army’s Adjutant-General, John Andre, frequently met with Simcoe at the Townsend house. And since it was The Culper Ring who tipped Washington off to Andre’s plot with the rebel traitor Benedict Arnold — to hand the American fort at West Point over to the British — some believe that Sally must have overheard Andre telling Simcoe about the plan and then relayed that information to her brother. (Although the story wasn’t told until a century later, and it seems like the dates don’t quite match up.)

In any case, looking back on Simcoe's lovelorn winter on Long Island, it seems that Sally's interest in him may have been nothing more than a rebel ruse. As the daughter of a revolutionary family, she did have plenty of reason to hate the British officer who was making himself at home in her house. And it can't have helped that he chopped down her family's beloved apple orchard so he could use the wood to build defences for a nearby fort. In the end, as you might expect, Sally Townsend rejected Simcoe’s plea to take him as her Valentine. In fact, she would never marry — she died as a single woman at the ripe old age of eighty.

Simcoe wouldn't have to live with that rejection for long: his days with the Townsends were numbered. Later that same year, he was captured in an ambush and spent six months in a rebel prison. There in his dank cell, his health began to fail him. He was eventually released in a prisoner exchange so he could head home to England and recover. It was there, as he convalesced at this godfather's country home, that he met a new love interest.

His godfather's niece Elizabeth was young and smart and pretty and curious, a strong writer and a wonderful artist. The two fell in love as she nursed him back to health and as they enjoyed long walks and romantic horseback rides through the rolling green hills of Devon. By the time Simcoe was chosen to serve as the first governor of Upper Canada, they were married. They headed off to the frontier together, where they would found the city we call Toronto.

But there is still one physical trace of Simcoe's lost love affair that survives to this day. You'll find it on Long Island, in the old Townsend house in Oyster Bay — their home is now open to the public as the Raynham Hall Museum. There, in the house where Simcoe once fell in love with his rebel spy, they've preserved a pane of glass from her bedroom window. There's a wistful message scratched into its surface — a few longing words of love thought to have been inscribed by the besotted British officer John Graves Simcoe: to "the adorable Miss Sally Sarah Townsend."

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If you're interested in stories about love and the history of Toronto, then you might be interest to know that my new book, The Toronto Book of Love, has been published by Dundurn Press. You can get it now from all the usual places — including the Dundurn site!

Brexit, Eton & The History of Toronto

The most famous boarding school in the world just got a little bit more famous. Thanks to the shocking result of the Brexit referendum, Eton College has been popping up in the news quite a lot in recent years. The posh boarding school is where two of the architects of the mess spent their teenage years. Both former Prime Minster David Cameron and former Mayor of London Boris Johnson graduated from Eton in the early 1980s. And now — three years after the referendum — Boris will become the new Prime Minister, elected as Tory leader on a promise to ram through Brexit no matter what toll it takes on the country.

So if you want to understand the breathtaking, aristocratic entitlement that has led the United Kingdom into self-inflicted disaster, it helps to understand Eton. And in understanding Eton, you can also better understand the history of Toronto — because it's not just where Boris and Dave went, it's where the man who founded our city went, too.

Eton sits on the banks of the River Thames, not far outside London, just across the river from Windsor Castle. It was founded all the way back in the 1400s; King Henry VI started the school as a charity meant to provide free education to the poor.

But oh how things have changed since then. In recent centuries, Eton has made its reputation by catering to the children of the rich and powerful, helping to perpetuate the strict British class system. Yearly tuition can cost as much as the equivalent of $60,000 in Canadian currency. For a long time, the school's official uniform was literally a top hat and tails. (They finally ditched the top hat in the 1960s, but they've kept the tails.) The school is synonymous with the idea of British entitlement: that the children of the country's ruling class should naturally become its next generation of rulers.

Nineteen British Prime Ministers have been students at Eton. Both Prince Harry and Prince William went there, too. So did George Orwell and Aldous Huxley and Percy Shelley and John Maynard Keynes. And if you're counting fictional characters, then so did James Bond and Captain Hook and Lord Grantham from Downton Abbey. 

Eton College

And so, it's not surprising to find that two of today's most powerful Conservative politicians both went to Eton, too. The old Prime Minster, David Cameron (inept champion of Remain), and the new Prime Minister, Boris Johnson (Leave-supporting buffoon), both graduated from Eton in the early 1980s. They say you can trace the roots of their rivalry all the way back there — and with it, some of the very beginnings of the Brexit disaster.

As a student, Boris was older, more popular and more successful than Cameron — things that mattered even more than usual at such an aristocratic school. And since Johnson did better at Eton — and then again when both young men attended Oxford University — they say it drove him nuts that Cameron had risen to greater heights since then. Boris might have been the former Mayor of London, a Member of Parliament, and a newspaper columnist who got paid more than £250,000 last year (or "chicken feed" as he calls it) for writing one article every week — but that, apparently, wasn't enough.

"Yes," Sonia Purnell writes in The Independent, "the fact that Cameron was two years below him at Eton – a terrifically hierarchical school – rankles deeply. As does the fact that it was Boris who shone there, not Cameron. Masters recall Johnson as a remarkable teenager. They do not recall Cameron at all."

According to countless media reports, Boris made it his mission to topple his old friend Dave and take his place as Prime Minster. If that meant joining the Leave campaign... well, that's what he was willing to do — whether or not he actually believed that leaving the European Union was a good idea for Britain.

Meanwhile, some suggest that Cameron's lifelong sense of entitlement — reinforced by his time at Eton — gave him a false sense of his own superiority. Slate describes him as "an establishment man through and through... the sort of person who gets away with too many things and comes to mistake his privilege for innate luck." When given the chance to gamble the future of his country in return for his own personal political gain, he did so. After all, he's been getting his way his entire life. Why would this time be any different? In order to appease the lunatic far-right fringe of his party, Cameron agreed to hold the Brexit referendum, confident that a Leave vote would never actually happen.

Boris and Dave

But when Boris — who is thought to have personally reassured Cameron that he would never support the Leave campaign — betrayed his old friend, things suddenly became much more complicated. Johnson's support gave legitimacy to the Leave faction, even while it descended into absurd lies and bigoted violence. The racists behind Brexit never would have won, according to The Daily Beast, "without the fig leaf of Boris's charm."

The result: a stunning victory for the Leave campaign, an economy in disarray, bigotry and xenophobia on the rise, the murder of an MP, the end of Cameron's career, and scenes of Boris Johnson being booed the moment he poked his head outside his front door. The Old Etonians had suddenly become two of the most hated men in the country they were raised to rule.

At first, it looked like Johnson's plan hadn't even worked: betrayed, in turn, by one of his own supporters (die-hard-Brexiter Michael Gove), Johnson was been forced out of the race to replace Cameron as PM. Theresa May won instead.

But now, Johnson's spectacular self-serving maneuverings have finally paid off: Boris has won the Tory leadership contest to replace May and will take over as the new Prime Minister.

The power of Eton College hasn't just been limited to British politics, either. Thanks to the Empire, the school's reach has historically extended far beyond England's own borders. In Toronto, you can trace Eton's influence all the way back to the founding of our modern city. More than two hundred years before Boris and Dave, there was John Graves Simcoe.

Simcoe went to Eton in the 1760s. And he too bought into its aristocratic vision for Britain. Years later, when he became the first Lieutenant Governor of Upper Canada, he was determined to make that aristocratic heritage an important part of his new province.

Before he sailed for Canada, Simcoe got in touch with another Eton graduate: the famous scientist Sir Joseph Banks. In his letter, Simcoe asked for any advice Banks might be able to offer, and laid out his vision for his new Upper Canadian capital: the city that would eventually become Toronto.

A strict class system, he insisted, would play a vital role. Simcoe didn't trust the general public; they couldn't be allowed to have real power. As a solider, he'd seen the bloody results of the American Revolution with his own eyes — and more recently, he'd heard the terrifying reports coming out of Paris during the French Revolution. In fact, the Reign of Terror began the very same summer Simcoe founded Toronto. In his experience, when the people gained power, they had a nasty habit of beheading the elites. And so Simcoe was determined that his new city would be free from what he called "tyrannical democracy."

"There are inherent defects in the congressional form of Government," he wrote in his letter to Banks, "the absolute prohibition of any order of nobility is a glaring one. I hope to have a hereditary council with some mark of nobility."

John Graves Simcoe

He would never quite get his wish: Toronto never developed an officially aristocratic system like the one they had back home in England. But Simcoe did make sure that power rested in the hands of a few loyal Tory families. For the first few decades of our city's history, families like the slave-owning Jarvis clan kept all of the best government jobs and appointments for themselves and their friends. The habit would eventually earn Toronto's ruling class a derisive nickname: The Family Compact.

With the backing of their British overlords, the Family Compact dominated the Legislative Assembly, blocked all democratic reform, and cracked down on dissent. Anyone who disagreed with the Tory elite or demanded change quickly found themselves subject to threats and intimidation — sometimes even violence or imprisonment.

The Family Compact had no doubt they were meant to be the natural rulers of the province — a sense of entitlement that would look familiar to anyone who has been following Boris and Dave during the Brexit fiasco.

To help ensure that the power of the Family Compact would continue long into the future, they even founded a Torontonian version of Eton. It's still around today: Upper Canada College. The school's own website describes it as being "modeled after the great public schools of Britain [what we call private schools in Canada], most notably Eton College." UCC's job would much be the same as Eton's job on the other side of the Atlantic: training the sons of the rich and powerful to become the new generation of elites.

And it worked. As Wikipedia points out, "The school has produced six lieutenant governors, four premiers, seven chief justices, and four Mayors of Toronto." There have been plenty of other rich and powerful graduates, too, like Michael Ignatieff, Ted Rogers, Galen Weston and Ken Thomson. In Toronto, the Old Boys of Upper Canada College have played something of a similar role to that of the Old Etonians in England.

But not everyone in Toronto was happy with the Family Compact. There was plenty of resentment against the ruling class in those early years. The opposition gained momentum over the city's first few decades, building into a reform movement led by the radical newspaper publisher and first Mayor of Toronto, William Lyon Mackenzie. He was becoming increasingly frustrated by the lack of democracy in Upper Canada. He made appeal after appeal to the British government, but his complaints fell on deaf ears — which was maybe not entirely surprising: nearly all of the British Prime Ministers during that period were Old Etonians themselves.

William Lyon Mackenzie

In the end, Mackenzie finally gave up on trying to find a peaceful solution; after a disappointing trip to London, he became convinced that revolution was the only way to break the Family Compact's grip on power. In 1837, he gathered an army north of Toronto and marched down toward the city with the aim of overthrowing the government.

Even the street the rebels marched down was a reminder of Eton's influence. Simcoe named the biggest road in Toronto after another one of his Old Etonian friends: Sir George Yonge.

In the end, of course, Mackenzie's rebellion failed. Democratic reform came peacefully a decade later under the name of Responsible Government. The leading champion of the cause was the moderate Robert Baldwin, who had been educated by the leader of the Family Compact. And Baldwin was able to convince the British of its value thanks in part to the support of Lord Durham, yet another Eton graduate. Change didn't come to Canada until the people advocating for it were members of the old boys club themselves.

More than a hundred and fifty years later, you can still see some echoes of that seminal divide in the Toronto politics of today. We saw it on stunning display in recent years, when Rob Ford was able to frame his mayoral campaign as a campaign against the "elites" by positioning himself as an outsider and purposefully distancing himself from the traditional, Upper Canada College-style Tories. Those who felt ignored by the establishment voted for Ford in droves. Casting a ballot for an apparent outsider seemed like a rare opportunity to give voice to their anger. Now his brother Doug has done the same, becoming Premier of Ontario.

In 2016, we saw similar emotions lead to similar results in the United Kingdom. The Leave side denounced the experts and vilified the establishment even though the leaders of the Leave campaign were establishment figures themselves. Boris Johnson has made a career out of playing the blond buffoon, a carefully crafted image, trying to seem like a man of the people instead of a millionaire raised in privilege. The Brexiters, much like Ford, managed to convince vast numbers of people that the real cause of their problems was a dastardly combination of expert opinion and immigration. Not, say, the damaging policies those very same Conservative politicians have been hawking for decades: like tax cuts for the rich paid for by service cuts for everyone else. 

Both campaigns were illusions. Rob Ford was a millionaire born into a political family. His policies were the same old Conservative policies that have been hurting the working class for years. His successor, the aptly-named John Tory, is one of the most establishment-friendly politician you could possibly imagine — and in general his policies are usually in line with those Ford was pushing. Even a vote against the establishment led to establishment-friendly policies; they were just served with a side of crack cocaine.
 

Six thousand kilometers and an entire ocean away, angry Britons voted in protest against their own elites, unleashing a wave of bigotry and decimating their nation's economy in the process. They have managed to drive one establishment-friendly leader out of power: Cameron, forced to resign in disgrace, will be remembered as one of the worst Prime Ministers in modern British history. But they replaced him with another contender to that title: Theresa May. And now they've replaced her with Cameron's old schoolmate Johnson, yet another establishment-friendly Tory leader moving into 10 Downing Street, ready to pick up right where the last one left off.  

The Old Etonian is dead. Long live the Old Etonian.

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Via Viv Lynch on Flickr

This post was originally published in 2016 — in the week after the Brexit referendum — and has been updated on July 23, 2019 to reflect Boris Johnson's victory in the Tory leadership contest to replace Theresa May.

You can learn more about the connection between the histories of Toronto and England with A Torontonian Historical Map of London here. Read more about Simcoe's vision for Toronto here. And more about Mackenzie's failed mission to London here.

There's a whole dramatized documentary about Johnson and Cameron's early years, "When Boris Met Dave," which you can watch on Vimeo here.

The main image of "Toffs and Toughs" via Rare Historical Photos here.  Photo of Boris and Dave via The Sun. Photo of Eton College by me as part of The Toronto Dreams Project's UK Tour, which explored the connections between the history of Toronto and the United Kingdom.

John Graves Simcoe's Weird Relationship With Slavery

Meet John Graves Simcoe. Founder of Toronto. British veteran of the American Revolution. And an avowed abolitionist with a very weird and complicated relationship to slavery.

Simcoe hated it. Back home in England as a Member of Parliament, he gave anti-slavery speeches in the House of Commons. And when he was picked to be the first Lieutenant Governor of Upper Canada, he made it clear: he saw no place for the practice in his new province. "The principles of the British Constitution do not admit of that slavery which Christianity condemns," he wrote before he officially took his post. "The moment I assume the Government of Upper Canada, under no modification will I assent to a law that discriminates by dishonest policy between natives of Africa, America or Europe." 

And indeed, one of the very first things Simcoe did when he got to Upper Canada was to introduce a bill to end slavery in the province forever. In July 1793, his "Act Against Slavery" became the very first slavery-abolishing law ever passed anywhere in the British Empire. To this day he's celebrated as the man who ended slavery in Upper Canada — more than 40 years before it was abolished across the Empire and 70 years before the Emancipation Proclamation in the United States.

But things weren't quite as simple as that makes it seem.

For one thing, Simcoe's law wasn't nearly as groundbreaking as it sounds. By the time he came to Canada, there were no slaves in England — a court decision had freed them all fifteen years earlier. Compared to the Mother Country, the Canadian colonies were behind the times. Hundreds of slaves were "owned" by the colonists in Upper Canada, many of them brought north to the new province by Loyalist refugees as they fled the revolution in the United States. The British government had actually encouraged the practice, passing a law in Westminster that promised new Canadian settlers they would get to keep their slaves.

So while slavery in England was already over, if Simcoe wanted to get rid of slavery in Upper Canada, he was going to have to pass a new law to actively abolish it. And that wasn't going to be easy.

Simcoe would need support. The bill would have to pass through the Legislative Assembly and then through the Legislative Council. Both of those bodies were full of slave owners. And that, in part, was thanks to none other than John Graves Simcoe.

Peter Russell tries to sell
Peggy & Jupiter Pompadour

The Legislative Assembly was an elected body. But the members of the Legislative Council were hand-picked by Simcoe himself — it worked a bit like the Senate does today. And Simcoe packed his Council full of slave-owners. At least five of the nine members were either slave-owners or from slave-owning families. They formed a majority. Simcoe, determined to abolish slavery in Upper Canada, had made it almost impossible to do.

But he was still going to try. It was the resistance of Chloe Cooley that gave him the opportunity he needed. Cooley was a Black woman living in slavery at Niagara. When her "master" sold her to someone on the American side of the river, he tied her up with rope and forced her into a boat to be taken across the border. Cooley, like many slaves, had long resisted her captivity: refusing work, stealing, disappearing for periods of time, generally trying to disrupt the life of her "master" and ensure her enslavement was as much of an inconvenience as possible. Now, she resisted again. As she was unloaded and handed over to her new "owner," Cooley screamed and put up a fight.

When Simcoe heard the tale, he was appalled — and he saw his chance. During the next session of the legislature, he pushed a bill to abolish slavery.

 
But with his government full of slave-owners, he was forced into a compromise — the exact thing he had promised never to do. The new law didn't abolish slavery immediately; instead, it would be gradually phased out. No new slaves could be brought into Upper Canada, but any who were already here would spend the rest of their lives in slavery. Their children would be born into captivity, too; they wouldn't be free until they turned twenty-five. Finally, anyone who wanted to free a slave was discouraged from doing so: they would be forced to provide financial security to ensure the newly freed slave wouldn't be a drain on the resources of the state.

The bill was passed just a few weeks before Simcoe founded Toronto. And so, the foundations of our city were laid with the help of slave labour. During the early years of the new town, there were fifteen Black slaves within its borders — and another ten just across the Don Valley.

Some of Toronto's slave owners are still familiar names today. William Jarvis is remembered by Jarvis Street; James Baby's old estate on the Humber River is still called Baby Point. Peter Russell — a gambling-addict ex-con who Simcoe trusted as Receiver- and Auditor-General — enslaved a woman named Peggy Pompadour and her three children: Jupiter, Amy and Milly. Their acts of resistance were brutally punished by Russell: Jupiter was once bound and strung up in the window of a storehouse as a painful public humiliation. But Peter Russell is still remembered in the names of Peter Street and Russell Hill Road.

Simcoe's relationship with slavery only got weirder and more conflicted after he left Toronto. In 1796, ill-health forced him to sail home to England. Just a few months later — while still officially serving as Lieutenant Governor of Upper Canada — John Graves Simcoe was sent to Haiti. There, the avowed abolitionist was asked to put down the biggest slave uprising since Spartacus.

Haiti was a French colony back then; they called it Saint Domingue. The leaders of the French Revolution had abolished slavery, but French royalists still controlled Haiti — and they had no intention of giving up their half a million slaves.

Toussaint L'Ouverture

When the slaves rose up in a revolution led by François Dominique Toussaint L’Ouverture, the French royalists asked the British for help. Thousands of British troops were sent to the island, hoping to crush the uprising, restore slavery, and secure the island's sugar riches for themselves. By the time Simcoe arrived, they'd been fighting for years without making any real progress. His job was to turn things around. He was appointed as commander of the British forces in Haiti — a man who hated slavery fighting a bloody war to preserve it.

The Haitian Revolution was a long and brutal struggle. It raged for thirteen years and claimed hundreds of thousands of lives. Countless atrocities were committed. Simcoe's attempt to keep his own men in check — an order to halt all "cruelties and outrages" — was ignored. His army pushed Toussaint's forces back, but were stalled by a counterattack. His men were dying by the thousands: some in bloody battles, still more of yellow fever.

Simcoe only lasted a few months before he got sick of fighting for a cause he didn't believe in. He was sick of the war, sick of a lack of support from his superiors, sick of literally being sick. He left Haiti and sailed home to England, where he tried to convince the government to withdraw from the war; he was nearly arrested for desertion. The British kept fighting for a year after Simcoe left Haiti, and the French kept fighting long after that. In the end, the Haitian Revolution was successful — it led to the establishment of a new, independent, slave-free country in 1804.

But while slavery was now over in Haiti, it was still part of life in Toronto. It would take many years before it gradually dwindled out: one by one the city's slaves died or were freed by their "masters." There's no record of when the practice finally ended in Toronto, but there were no slaves left in the city by the time the British abolished slavery across the Empire on August 1, 1834.

By then, Toronto was beginning to gain a very different reputation. Black families like the Abbotts, the Blackburns and the Augustas — some of them former slaves themselves — worked with White allies like George Brown to make Toronto a relatively safe haven for those fleeing slavery in the United States. They organized anti-slavery societies, secured lodging for refugees, and raised funds to help the new arrivals get started in their new home. They struggled every day to make Toronto a more welcoming place for those fleeing racial persecution.

Half a century after Simcoe's chilling compromise, Toronto had become an important stop at the end of the Underground Railroad.

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A version of this story will appear in The Toronto Book of the Dead Coming September 2017 Pre-order from Amazon, Indigo, or your favourite bookseller

This post was based in part on a Twitter essay I tweeted out on Simcoe day last year, which you can find here.

You can learn more about John Graves Simcoe from "John Graves Simcoe, 1752–1806: A Biography" by Mary Beacock Fryer and Christopher Dracott (which is available from Amazon here or the Toronto Public Library here), from his entry in the Dictionary of Canadian Biography here, and from his entry entry in the Canadian Encyclopedia here. And you can read his letters in "The Correspondence of Lieut. Governor John Graves Simcoe" which you can find at the Toronto Public Library here.

Learn more about slavery and resistance in Upper Canada from Natasha Henry's "Talking About Freedom: Celebrating Emancipation Day in Canada" (Amazon here, Toronto Public Library here), from Robin Winks' "The Blacks in Canada: A History" (Amazon here, Toronto Public Library here), from "The Underground Railroad: Next Stop, Toronto!" by Adrienna Shadd, Afua Cooper and Karolyn Smardz Frost (Amazon here, Toronto Public Library here), from William Renwick Riddell's 1923 article in the Journal of Criminal Law and Criminology here (that's a PDF), or from the Canadian Encyclopedia here. The Encyclopedia also has an entry about Chloe Cooley and Simcoe's law here. 

You'll find the Wikipedia entry for the Haitian Revolution here. And a timeline of the history of Haiti here.

Read some my previous posts about the Simcoes:
The story of John Graves Simcoe's vision for Toronto (a city so awesome it would undo the American Revolution)
The story of Elizabeth Simcoe's 1794 nightmare 
The story of their dog, Jack Sharp 
The story of their cat 
The story of how they fell in love and the magical hills where it happened 
The story of their summer home in Budleigh Salterton 
The story of their connection to Samuel Coleridge and his family 
The story of the Simcoe family and Exeter and death

This post is related to dream 01 Metropolitan York John Graves Simcoe, 1793

This post is related to dream 18 Russell Creek Peter Russell, 1799

Simcoe's Weird & Complicated Relationship With Slavery — A Tweetstorm

August 1 was both Simcoe Day and Emancipation Day in the City of Toronto. One is meant to remember the British soldier who founded our city; the other marks the day slavery was abolished across the entire British Empire. It's an interesting overlap: Simcoe was responsible for abolishing slavery in Toronto; he passed the first law to end the practice ever passed anywhere in the Empire. But his relationship to slavery wasn't anywhere near as clear-cut and simple as that might make it sound. And so, to mark this year's Simcoe and Emancipation Days, I thought I'd do some tweeting.

You'll find the Twitter essay embedded below. And if you can't see it for any reason, you can read it all on Storify here.

John Graves Simcoe, Napoleon Bonaparte & The Politics of Horse Shit

This is a photo of horse shit. But it's not just any photo of horse shit. This horse shit is on Woodbury Common — a beautiful patch of heathland in the English countryside. And with horse shit on Woodbury Common, you can tell a story about the founder of Toronto — John Graves Simcoe — and about a man who challenged him to a duel over that dung.

This was a few years after Simcoe founded Toronto. He'd come back home to England by then, returning to his country in a deeply troubled time. England was at war with France.

The French Revolution had started many years earlier; it was already well underway by the time Simcoe and his family left home for Canada. But things had gotten even bloodier while they were gone: Simcoe founded Toronto in July of 1793; the Reign of Terror began just a couple of months after that, while the Simcoes were living in a pair of fancy tents pitched at the mouth of Garrison Creek. 

And even there — six thousand kilometers from the guillotines of Paris — news of the atrocities reached them. In August, the Simcoes were visited by a pair of fleeing French aristocrats hoping to settle in Upper Canada. They told a morbid story about King Louis' botched attempt to escape his captors. By the time they shared that anecdote, the French king had already lost his head.

A few months later, Marie Antoinette followed her husband to the guillotine. News of her death took many weeks to travel across the Atlantic and up the St. Lawrence to the Canadian frontier. When it did, Simcoe marked the occasion with solemn respect. That evening, the settlers of Toronto dressed all in black, postponing the dance they had planned for the night. They might hate the French, but they were staunch monarchists — many of them had already suffered through the horrors of the American Revolution and were deeply upset by the idea of yet another bloody, democratic uprising.

It was a frightening time. The French Revolution sparked decades of war between France and the monarchies of Europe, including Britain. At the very same time that Simcoe was busy planning the first few blocks of Toronto, he was also busy worrying that the war back home would spread to North America. Even now, French revolutionaries were stirring up trouble in the United States, trying to get the Americans to join the war and invade Canada. Some had even travelled into Québec, where they hoped to convince the French Canadians to rise up and launch their own revolution. As the Simcoes slept in their tents at night, they worried that at any moment an enemy ship might sail over the horizon — or enemy soldiers burst from the woods. Simcoe's wife, Elizabeth, had nightmares about it.

John Graves Simcoe

Things only got scarier when they began to head home for England. As the Simcoes sailed out of the mouth of the St. Lawrence River, French warships were waiting. They chased them out into the Atlantic, seizing other English vessels who were sailing nearby. As the Simcoes' ship dodged icebergs off the coast of Labrador, Elizabeth and the children hid themselves in the cramped quarters below deck. They could hear guns in the distance. It took weeks to sail across the open ocean before the Simcoes finally reached the safety of home.

Even then, it wasn't over. The British would be at war with the French for most of the next twenty years. And things would only get worse. By the time the Simcoes got back to England, a new French general had begun to make a name for himself. Napoleon Bonaparte would prove to be one of the most brilliant and most power hungry dictators in history.

The wars against the French would dominate the rest of Simcoe's life. In the end, he would die fighting them.

But first, he had an important role to play. Simcoe didn't always get along with his superiors, but he did earn the respect of some of the most powerful men in England: Prime Minister Addington, Admiral Nelson, the Duke of York; he even spent time with "Mad" King George. His experience was especially respected when it came to military matters. He'd been one of the most celebrated heroes on the British side of the American Revolution. And as the first Lieutenant Governor of Upper Canada, he'd been responsible for preparing the defences of the new province in case of an American invasion. And so, just a couple of years after his return to England, Simcoe was given a new job: preparing part of England in case of a French invasion.

At times, it seemed as if that invasion could happen at any moment — especially once Napoleon was in charge. Having already expanded his empire on the Continent, the French general began to assemble an army to bring England to its knees. Two hundred thousand men were being trained on the coast of France: the Armée d'Angleterre. A whole flotilla of barges was built to carry them across the English Channel. For a while, Napoleon was even toying with the idea of deploying the world's first air force: a fleet of hot air balloons to support the attack. There were rumours of a giant tunnel being dug beneath the Channel. And of a massive raft powered by windmills. To pay for it all, Napoleon had already sold the Louisiana Territory to the Americans. He was so sure his invasion was going to succeed that he built a triumphal arch to commemorate it before it had even happened.

Meanwhile, on the other side of the Channel, Simcoe was getting ready for the invasion. The British government had put him in charge of the entire defence of the West Country. Devon, Cornwall and Somerset would be under his command. If the French landed there, Simcoe and his men would answer with a scorched earth campaign. They would evacuate all women and children, the elderly and the sick — and all the livestock, too. Everything they left behind would be destroyed. The French would find nothing to eat.

Instead, they would be met by the biggest military force Britain had ever assembled. More than six hundred thousand men were ready to fight — nearly 10% of the entire population of England. In the West Country alone, Simcoe was in command of twelve thousand men.

Woodbury Common

But they weren't all experienced soldiers. Professional troops were joined by volunteers and conscripted militia. They needed lots of training. And to do that training, Simcoe sometimes took them to Woodbury Common.

Woodbury Common is high in the gorgeous green hills of Devon. It's just a few kilometers from the Simcoes' summer home in the seaside town of Budleigh Salterton. And it's not too far from their country estate in the Blackdown Hills, either. It's a beautiful place: gently rolling hills covered with flowers, shrubs and short grass. It's typical heathland; in fact, if you look up "heath" on Wikipedia, the first photo you'll see is a photo of Woodbury Common. It's one of England's official Areas of Outstanding Natural Beauty.

At the very highest point on the Common, you'll find a patch of trees. They're growing on the remains of massive earthworks. The big ditches are what's left of the ancient Woodbury Castle: an Iron Age hill fort built in the days of the druids; it's more than two thousand years old. From the lands around the castle, you can see for miles and miles in every direction — all the way back down to the sea. It's the perfect spot for a military base. In fact, the British army still trains there to this day.

And so about two hundred years ago, you could find thousands of Simcoe's troops camping on Woodbury Common as they awaited Napoleon's arrival — and with those camping men came hundreds of horses.

That, finally, bring us to the horse shit.

With all those horses trotting around, there was, of course, plenty of dung on Woodbury Common. And the question of who was ultimately responsible for it — Simcoe's troops or the local land owner — sparked a fight that nearly ended in a duel. But not for the reason you might think.

The principal owner of the lands around Woodbury Common was a man by the name of Lord Rolle. History would eventually remember him as the man who tripped during Queen Victoria's coronation and rolled down the steps to the throne. He and Simcoe didn't get along at all. Rolle was pretty pissed off by the inconvenience caused by all the men camping on the Common. And he was even more pissed off by the fact that they were cleaning up after themselves. Simcoe was making sure that all the horse shit was being collected and taken away. Rolle was furious. He wanted that horse shit for himself. It was valuable manure.

Rolle began a letter-writing campaign. He complained to the authorities, insisting that tradition dictated that any horse shit left by the military on common land belonged to the local lord of the manor: him. Simcoe was stealing his shit. And if Simcoe got away with it, it would set a dangerous precedent: any British general would be allowed to trample the rights of any lord. The question of the horse shit on Woodbury Common, Rolle argued, was a question of importance to every single subject in the British Empire.

Simcoe, for his part, sent a flurry of his own letters arguing the opposite. And as the letters flew back and forth, the fight escalated. Before long, Rolle was ordering his men to physically stop Simcoe's troops from removing the shit from the Common. The dispute was getting so serious that it was eventually forwarded all the way to the man in charge of the entire British military: the Duke of York (the son of "Mad" King George III and the guy who Simcoe had originally named Toronto after — back when it was still known as the town of York).
 

Woodbury Castle

In the end, Simcoe lost the battle of the Woodbury Common horse shit. His orders came directly from Whitehall — the heart of the British government at Westminster. The manure belonged to Rolle. He would be compensated for the shit that had already been taken away. And he would be allowed to keep any dung produced by Simcoe's horses in the future — as long as he sold it to the public at an appropriate discount.

But Rolle still wasn't satisfied. He was so angry with Simcoe that he challenged him to a duel. He wanted, he declared, to have a fist-fight with the founder of Toronto.

 
Simcoe was not impressed. Gentlemen, he replied, didn't fight with their fists. It was unseemly. If Rolle wanted to have a duel, they could have a duel: with pistols or with swords. It didn't count if there was no chance you might die.

Rolle backed down.

And so did Napoleon. The tiny French Emperor never did invade England. Instead, he marched his army east into the heart of Europe. But it wasn't the end of Simcoe's connection to the man. There was one sad chapter left to come.

It didn't take long for the French army to invade Spain and Portugal. The Peninsular War — as it was called — would rage for years on end. It was a bloody campaign. Tens of thousands were killed or wounded. Simcoe's own son, Francis, would die during the Siege of Badajoz in Portugal. (Just a toddler when Toronto was founded, his parents had jokingly named their log cabin in his honour: Castle Frank. We still remember it today in the name of a subway station.)

By then, John Graves Simcoe was already dead. He died during that same campaign. His preparations for Napoleon's invasion had earned him a promotion: Commander-in-Chief of the entire British army in India. But just before he left for his new post, he got new orders: his services were once again desperately needed in the fight against the French. Simcoe sailed to Portugal. But the ship he sailed on was damp and newly painted. He had always suffered from terrible respiratory problems — in fact, that's why he'd been forced to come home from Canada.

Simcoe was deathly ill by the time he made it to Lisbon. He would never recover. He was loaded back onto the same sickly ship and sent home across the Channel to England. He died in Exeter just a few days later.

As for Napoleon, well, he did finally make it to Devon one day. But it wasn't at the head of an invading army. Instead, he saw those rolling green hills from the deck of a British ship as it sailed by. It was all over; he'd lost the Battle of Waterloo and was now being held prisoner. Defeated for the final time, the French general asked if he could retire in England with a small parcel of land. His request was refused. The British didn't let him off that ship; he was never to set foot in Devon. Instead, they kept sailing, taking him far away to the isolated island of Saint Helena where he would live out the rest of his days in peace and frustrating quiet.

-----

More than two hundred years after Simcoe founded our city, Toronto is still wrestling with the question of who is responsible for our horse shit. You can read more about that on the CBC News website here.

Read more of my posts about the Simcoes: the story of John Graves Simcoe's vision for Toronto (a city so awesome it would undo the American Revolution); the story of Elizabeth Simcoe's 1794 nightmare; the story of their dog, Jack Sharp; the story of their cat; the story of how they fell in love and the magical hills where it happened; the story of their summer home in Budleigh Salterton; the story of their connection to Samuel Coleridge and his family; the story of the Simcoe family and Exeter and death.

The first person to alert me to the story of Simcoe and the shit was Michael Downes at the Fairlynch Museum in Budleigh Salterton. You can find the museum at their website, on Twitter, and on Facebook.

Simcoe's biographers, Mary Beacock Fryer and Christopher Dracott, cover the story in their book, which you borrow from the Toronto Public Library here or buy here.

You can learn more about Napoleon's brief stay in Devon in Devonshire Magazine here.

Photos of Woodbury Common and Woodbury Castle by me: Adam Bunch.

This post is related to dream 01 Metropolitan York John Graves Simcoe, 1793

This post is related to dream 30 The Conference of the Beasts Francis Simcoe, 1796

This post is related to dream 34 The Upper Canadian Ball Elizabeth Simcoe, 1793

UK Tour Photos: Northamptonshire, Birthplace of the Simcoes

A year later, I'm still posting photos from the Toronto Dreams Project's UK Tour. I hadn't originally planned on visiting Northamptonshire, but upon my arrival in England, I was invited to spend a day in the lovely county of spires and squires. It's the part of the country where both John Graves Simcoe, the founder of Toronto, and his future wife, Elizabeth, were born. It's a strange coincidence — despite being born within a few kilometers of each other, it seems they didn't meet and fall in love until many years later far away in the rolling hills of Devon.

My hosts for the day were Ioan and Alice Thomas. Ioan a retired biology teacher who used to work at the local Oundle School — he inspired one of his students to pursue a career in science: a boy by the name of Richard Dawkins. Ioan and Alice are both very interested in their local history, which means that they are both very interested in the history of the Simcoes. They were nice enough to show me around the countryside, stopping to visit some of the Simcoes' childhood haunts, including the churches they attended as children and the mansion where the founder of Toronto was born.

You can check out all of my photos from my day in Northamptonshire on Facebook right here:

FULL GALLERY

And, as always, you can follow me on Instagram at @todreamsproject.

Toronto's Founding Dog & How He Almost Got Eaten

It was the summer of 1793. The summer our city was founded. On an early Tuesday morning, as the late July sun rose above Lake Ontario, a British warship sailed into Toronto Bay. She was the HMS Mississauga. She had sailed overnight from Niagara, arriving in darkness, waiting for dawn and a local fur trader to show her the way through the treacherous shoals at the mouth of the harbour. On board was the first Lieutenant Governor of Upper Canada: John Graves Simcoe. His family was with him, too. The Simcoes had come to found a new capital for the new province: a tiny muddy town that would eventually grow into a booming metropolis of concrete and glass filled with millions of people.

The Simcoes weren't alone. They had brought their pets with them. There was a white cat with grey spots and a big friendly beast of a dog. He was a Newfoundland. His name was Jack Sharp.

Newfoundlands are a Canadian dog. By the time Jack Sharp was born, his breed had already been living on the island of Newfoundland for centuries. They've been there so long that no one is entirely sure where they came from — how they were first bred or evolved. Some people like to say they're descended from the big black bear dogs the Vikings brought with them across the Atlantic a thousand years ago. Others say their ancestors were the wild wolves of Newfoundland, or the domesticated hunting dogs of the local First Nations people. But most seem to think they were probably bred by the first European fishermen to come to Canada — sailors from the Basque Country and from Portugal who spent their summers fishing the waters off the coast of Newfoundland in the very early 1500s. However it happened, by the time the first colonists made the island their permanent home, the Newfoundland dog was solidly established as its own distinct breed.

They were perfect for life on the frontier. Big and strong and brave. Smart and loyal. They have webbed feet and a thick, waterproof coat, so they're fantastic swimmers. Just like their cousins the St. Bernards, they're famous for rescuing people. When the first European explorers headed west toward the Pacific, Newfoundlands were at their side — one travelled with the famous British-Canadian map-maker David Thompson; another with the Americans Lewis and Clark. The dogs became a familiar sight for Canadian pioneers.

The Niagara River by Elizabeth Simcoe, 1790s

Jack Sharp was one of those frontier dogs. He lived in Niagara-on-the-Lake back in the days when it was still a new settlement — so new it didn't even have a church yet; an isolated outpost at the spot where the Niagara River meets Lake Ontario. It was called Newark back then, a tiny town with a tiny population. But for a few brief years, it was the centre of political power in Upper Canada: the brand new capital of the brand new province, which had recently been created as a safe haven for Loyalist refugees in the wake of the American Revolution. 

The first Governor of the new province arrived at Niagara in the summer of 1792. It took John Graves Simcoe and his family nearly a year to make the long trip from England all the way out to the edge of the Canadian frontier. They spent two months sailing across the Atlantic, an entire winter stuck in Quebec City, and another two months travelling up the St. Lawrence and across Lake Ontario.

Back home in England, they'd enjoyed life on a sprawling country estate with a legion of servants to take care of them. At Niagara, life was much more rustic. They pitched a pair of elaborate tents on the banks of the river — the same canvas houses once used by the legendary explorer Captain Cook on his famous travels through the Pacific. The Simcoes still had plenty of help and lots of nice things, but life in Canada was much more difficult than it had been back home. The Governor's wife, Elizabeth, even suffered from a bout of malaria.

Still, the Simcoes did all they could to bring their British way of life to Upper Canada — that was, in fact, part of their mission. While the Governor busied himself running his new province, Elizabeth kept a detailed diary, painted watercolours, did needlework and entertained the most powerful Upper Canadian families. Her calendar was filled with social events: dinners, dances, balls and card games with people like the Jarvises, the Russells and Chief Justice Osgoode. Even Prince Edward, the future father of Queen Victoria, came all the way to Niagara for an official state visit. And there were visits from important First Nations allies, too, like the Mohawk leader Joseph Brant, Thayendanegea.

Elizabeth Simcoe

Elizabeth also had a family to run. The Simcoes had brought their youngest children with them to Canada: Sophia was in her terrible twos; Francis had just turned one. Even with a pair of nurses to help, the toddlers were more than a handful. And Elizabeth was pregnant yet again. That winter in the canvas house, she gave birth to a baby girl they named Katherine.

Even on the frontier, the Simcoe children would grow up with plenty of pets. Once they got to Upper Canada, the Simcoes had been given a white cat with grey spots and a hound called Trojan. Trojan was a gift for the kids, but it was Elizabeth Simcoe that he loved best. He even slept in her room inside the canvas house at night. And soon, there was another new addition to the menagerie. Jack Sharp had been the sheriff's dog. But when the Simcoes arrived, the big Newfoundland quickly fell in love with them. Before long, he had managed to adopt them as his own, joining their growing family. 

Elizabeth wrote about the animals in her diary — and about the mischief they caused. When Jack Sharp joined Governor Simcoe on a long trip to Detroit, the big dog faced off against a raccoon and then attacked a porcupine and earned a neck full of quills. When Elizabeth left Trojan alone in her tent with a map she'd painstakingly drawn, the hound tore it to pieces. (Governor Simcoe, who fancied himself something of a poet, even wrote some verses to mark the occasion: "Upon the Dog Trojan tearing the Map of N. America.")

Sadly, Trojan wouldn't live to see Toronto. He met a tragic end in the spring of 1793 — on a strangely hot day in early April. The heat was sweltering, recorded as high as 45°C. It was so hot that Trojan fell ill. When one of Simcoe's soldiers saw the symptoms, he made a terrible mistake: he thought Trojan had contracted rabies. He hadn't — if he had, he would have been scared of the water and wouldn't have waded out into the river to cool off like he did. But the soldier didn't know any better: he shot the dog dead.

So that summer, when the Simcoe family left Niagara, it was only their cat and Jack Sharp who came with them. 

They left because Niagara wasn't going to be safe anymore. Soon, the Americans would be taking over the other side of the river; it was one of the peace terms negotiated in the wake of the Revolution. The big guns of Fort Niagara were over there — just across the mouth of the river from Niagara-on-the-Lake. The tiny capital would be almost impossible to defend if the Americans decided to invade. And it seemed inevitable they would. Simcoe needed to find a new capital. Fast.

Toronto harbour by Elizabeth Simcoe, 1793

The spot he eventually picked was directly north across the lake from Niagara: a place called Toronto. There, a natural harbour had been formed by a long sandbar that would eventually become the Toronto islands. There was only one way into the bay, so it would be relatively easy to defend against an attack. That's where Simcoe would build his new capital.

In the middle of July, the Governor sent a hundred soldiers across the lake to begin work. They were the Queen's Rangers; some of them, the very same men Simcoe had commanded while fighting against the American rebels during the Revolution. At Toronto, his troops would build on land the British had "bought" from the Mississaugas years earlier (with a document so sketchy the Canadian government would eventually settle a land claim for $145 million). Simcoe's men made camp at a spot near the entrance to the harbour, at the mouth of what would become known as Garrison Creek. There, they got to work felling trees, hacking away at the ancient forest that towered over the shore. Great pines and oaks came crashing to the ground. In their place, a military base began to take shape: Fort York. It was the beginning a brand new town. Simcoe would call it York; we call it Toronto.

Back at Niagara, the Simcoes were getting ready to follow the Queen's Rangers across the lake. The Governor had just finished overseeing a session of the Upper Canadian legislature — one of the most important parliamentary sessions in Canadian history. Simcoe wanted to abolish slavery; the elected assembly balked. Slave-owning families like the Jarvises and the Russells were planning to bring their slaves with them to the new capital. Simcoe convinced them to accept a comprise: they could keep the slaves they already owned, but no new slaves could enter the province and the children of slaves would be freed when they reached the age of 25. The Act Against Slavery was the first law to abolish slavery in the history of the British Empire.

It was at the very end of that same month — on July 29th — that the Simcoes left Niagara. That night, the family and their pets climbed aboard the HMS Mississauga. She was a big warship: an armed schooner. An impressive way to travel — for a human or a dog.

As the Simcoes slept, the warship sailed north across the lake. Early the next morning, she made her careful way into Toronto Bay.

Toronto shoreline by Elizabeth Simcoe, 1796

It was the middle of the afternoon by the time the Governor and his wife went ashore for the first time. And when they did, they brought the dog with them.

Jack Sharp was far from the first canine to ever set paw on this land. Wolves and foxes roamed the woods around Toronto. And domesticated dogs had been here as long as humans had. The people of the First Nations and their ancestors had been hunting with them on the northern shore of Lake Ontario for thousands and thousands of years before our city was founded. As the Wendat-Huron historian George Sioui points out, dogs played an important role in the spiritual life of his own nation. The first racist French missionaries — anxious to paint the First Nations as "uncivilized" — claimed those dogs were only being raised for their meat. "Like sheep," they said. But in fact, dog meat was only consumed during important ritual ceremonies, and the people shared a close bond with their canine companions. The Wendat had long said that souls travel a path through the stars when they die: humans along the Milky Way and their dogs along a celestial dog path right next to them. In more recent years, as the first Europeans arrived, other dogs must have visited Toronto. Many of the explorers, fur traders and early settlers who passed through the area probably had dogs with them, too.
 
So Jack Sharp wasn't Toronto's first dog. Not by a long shot. But he was our city's founding dog: the canine member of the first family to establish the town that would grow into our modern metropolis.

A few days after they arrived, the Simcoes pitched their canvas houses just across the creek from Fort York, where they could watch as the Queen's Rangers hammered and sawed away. That's when they brought the children ashore, along with the nurses and servants. By the end of the first week of August, the entire family, including Jack Sharp, was living in the fancy tents at the mouth of Garrison Creek. In the months to come, the town itself would begin to take shape: the first ten blocks were carved out of the woods where the St. Lawrence Market neighbourhoood is now. From George Street over to Berkeley; from Front Street up to Adelaide.

It's easy to imagine what life in Toronto must have been like for Jack Sharp. Splashing in the shallows of the harbour as waterfowl scattered into the sky. Playing with the Simcoe children on the beach. Racing through the old forest, chasing chipmunks, rabbits and squirrels.

Toronto 1793 (with HMS Mississauga) by Elizabeth Simcoe

But for the humans, life on shore at Toronto was even harder than life at Niagara had been. There, at least, the settlers enjoyed an established town. Here, the town was still being built. Many of the province's other most powerful families were shocked by the Simcoes' living conditions. As Peter Russell wrote to his sister, "you have no conception of the Misery in which they live..." The other leading political families dragged their feet, staying at Niagara as long as they could before following the Simcoes across the lake.

The First Family of Upper Canada suffered through an entire winter at Toronto. But the most terrible moment of the Simcoes' time in Canada came the following spring. Katherine Simcoe had been a very healthy baby; she was more than a year old now, beginning to walk and to talk, old enough to start playing with the cat and Jack Sharp. But in April she suddenly fell very ill. It may have been malaria or some other similar disease. A fever turned into a terrifying night of uncontrollable spasms. By morning, she was gone. She was buried in a new cemetery near the fort; today, it's a park we call Victoria Memorial Square, just a bit south-east of Bathurst & King.

For the Simcoes, death was never far away. The previous fall, Jack Sharp had had his own brush with mortality. And Governor Simcoe, too.

It came during a long trip north. Simcoe wanted to find the best route from Toronto all the way up to Lake Huron. Easy movement through the province would be vital in case of an American invasion. And that was seeming ever-more imminent: the British were now at war with France, the Americans' allies, caught up in the violence that engulfed Europe in the wake the French Revolution. Simcoe was worried the trouble would spread across the Atlantic — which it soon would with the War of 1812. The Simcoes' peaceful life at Toronto felt precarious. Enemy ships might sail over the horizon at any moment; enemy troops might emerge from the woods. As she slept in her canvas house at night, Elizabeth had nightmares about it. In fact, when the Simcoes finally sailed home to England, French warships would be waiting to chase them out of the mouth of the St. Lawrence. Both John Graves Simcoe and his son Francis would eventually die in the fight against Napoleon.

So that September, Simcoe and his men headed north with the help of Ojibway guides. Jack Sharp went with them, too. They travelled up a portage route called the Toronto Carrying-Place. The big dog made for something of an awkward passenger in a canoe, but they made quick progress up the Humber River, through the marshlands far to the north of Toronto, and then along the Holland River to a lake the French called Lac aux Claies.

John Graves Simcoe

When they arrived, Simcoe renamed the lake, like he was renaming just about everything he found in Upper Canada. He called it "Lake Simcoe" — not after himself, but after his father, who had died in Canada during the last war against the French, just a few months before the Battle of the Plains of Abraham.

There, Simcoe found his route north. It wouldn't be hard to get from Lake Simcoe to Lake Huron — and to make things even easier, he would have a road built north from Toronto toward the Holland River. He named the road after a friend, the British Secretary at War: Sir George Yonge.

But getting home now — with Yonge Street still just a dream — would prove to be an unexpectedly perilous challenge.

As Simcoe, his men, his dog and the Ojibway guides all headed back south toward Toronto, their luck began to turn against them. One man had nearly severed a toe and couldn't walk anymore; others would fall ill. The party was forced to split up. The group Simcoe was with only had enough food for one day, but had a five-day journey ahead of them. From there, things quickly got worse. They were taking a different route home than the one they'd taken north: this time, they were heading along the eastern fork of the Toronto Carrying-Place portage route, which headed south down the Rouge River. They got lost along the way, stumbling through the woods for days on end, never quite sure where they were. Meanwhile, their rations were growing dangerous low. If they didn't find home soon, they would starve.

Things were getting desperate. So a plan took shape. If they didn't find Toronto that day, they would have no choice. They would kill Jack Sharp. And then eat him.

The Newfoundland was spared just in the nick of time. First, the men came across a surveyor's line. It was a good sign. And then, through the trees they spotted it: Lake Ontario. They finally knew where they were: just a few kilometers from the tiny new Upper Canadian capital. They were ecstatic. That morning, they wolfed down the rest of their food for breakfast and then finally headed west toward home.

The founder of Toronto was saved. And so was Toronto's founding dog. 

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That painting at the top of this post isn't Jack Sharp, but another famous Newfoundland dog called Bob. The painting is called "A Distinguished Member of the Humane Society" by Sir Edwin Henry Landseer, painted in 1831. Bob was found in a shipwreck off the coast of England and would go on to save twenty-three people from drowning in the Thames over the course of fourteen years.

You can read my post about the Simcoe's cat here, about Elizabeth Simcoe's nightmare here, and about John Graves Simcoe's vision for Toronto (a city so awesome it would undo the American Revolution) here.

You can read Elizabeth Simcoe's diary online here. You can borrow it from the Toronto Public Library here. Or buy it from Amazon here.

You can read excerpts from Elizabeth Simcoe biography, by Mary Beacock Fryer, on Google Books here, buy it here, or borrow it here from the Toronto Public Library. Her biography of John Graves Simcoe written with Christopher Dracott is here and here. While her biography of Francis Simcoe is here and here.

You can read Bathsheba Susannah Wesley's fascinating Master's thesis about her habit of setting small fires during her time in Canada here [PDF]. The always excellent Dictionary of Canadian Biography has a full bio for Elizabeth Simcoe here. And John Graves Simcoe here. You can learn more about the soldiers who built Toronto, the Queen's Rangers, here. And learn more about the Simcoe's canvas houses here.

Learn more about the historian George Sioui from the Tyee here. The New York Times has a history of dogs in the early Americas here. Cheryl MacDonald writes about Jack Sharp and other famous Newfoundlands in her book "Celebrated Pets" on Google Books here. Jack Sharp also gets mentions in a footnote to Richard D. Merritt's "On Common Ground: The Ongoing Story of the Commons in Niagara-on-the-Lake" on Google Books here.

Elizabeth Simcoe's painting of the Toronto harbour comes from the Toronto Public Library's Digital Archives here.  Her painting of the Toronto shoreline comes via Heritage Toronto here. Her painting of the Niagara River comes from the Wikimedia Commons here. 

This post is related to dream 01 Metropolitan York John Graves Simcoe, 1793

This post is related to dream 30 The Conference of the Beasts Francis Simcoe, 1796

This post is related to dream 34 The Upper Canadian Ball Elizabeth Simcoe, 1793