The sandbar stretched out into the lake, a long peninsula protecting a beautiful bay filled with water as clear as crystal. It was a peaceful place, where huge flocks of ducks and geese floated on rippling waves and loons called out in the distance. On the far side of the bay, a great forest rose up from the shoreline, with oaks and pines looming over the slight bluff that ran along the edge of the lake. There were bears, wolves, and cougars among those trees. At the back of the bay, a sprawling marsh was filled with long reeds and red-winged blackbirds whose full-throated trills pierced the air.
Standing out there on the sandbar, Elizabeth Simcoe could look across the water and see the beginnings of the metropolis to come. This is the place her husband had chosen to build his new city. The Simcoes had arrived just three months earlier, the new lieutenant-governor and his wife sailing into the bay with Rousseau’s help before coming ashore. They brought much of their family with them: three small children, a brave white cat with grey spots, and a big Newfoundland dog called Jack Sharp. By then, Simcoe’s men had already arrived: his soldiers pitched a few white tents near the mouth of a creek they’d call the Garrison, on a spot dwarfed by the leafy giants of the ancient forest. That’s where they’d begun the hard work of bringing those giants down, clearing the bush to make way for the construction of a military base. Fort York would defend the entrance to the bay, a stronghold ready for the day when the Americans invaded — John Graves Simcoe knew that war with the United States was inevitable. It was only a matter of time.
Eventually, the town would be built a few kilometres to the east, near the back of the bay, so that an invading army would have to sail past the guns of Fort York to attack it. A grove of fine oak trees would come crashing to the ground to make way for the first ten blocks of the new town. But for now, the Simcoes were living relatively rough. They owned a pair of tents that folded out to become a little canvas house — they even had wallpaper and wooden floors. This was far from the life of luxury Elizabeth Simcoe was used to. Back home in England, they lived on a beautiful country estate with an army of servants. But she was embracing life on the frontier. She liked the adventure. She enjoyed exploring the forests of Toronto, riding her horse out to the Humber River where the Rousseaus lived, rowing up the Don Valley or out by the Scarborough Bluffs, hiking through the woods to visit the ruins of Fort Rouillé, clambering over fallen trees and getting drenched in the rain. She had a freedom at Toronto she would never have back home in England.
On that particular November evening, the Simcoes had taken a canoe out across the bay to have dinner in a meadow on the sandbar. The peninsula had quickly become one of Elizabeth Simcoe’s most beloved places in the world — “my favourite sands,” as she put it in her diary. It had long been considered a place of healing by the local First Nations, and the lieutenant-governor’s wife found the crisp, clean air invigorating. She’d been a regular visitor ever since she’d arrived, venturing out across the long, low strip of land dotted with meadows and ponds where the ground was draped in flowers of purple and white. She rode her horse among the fir trees and the poplars wrapped in vines. The French had called it le presqu’ile de Toronto — the almost island of Toronto. And indeed, a few decades later, a series of great storms would batter away at the peninsula; the crashing waves washed the sand away until the connection to the mainland was severed. The sandbar became the Toronto Islands.
There may have been nowhere in the world Elizabeth Simcoe felt more free than out there on her almost island, thousands of kilometres from the drawing rooms of England, with their strict rules of etiquette and decorum. She was a proper English gentlewoman, but out here on the frontier, she could do things she would never feel comfortable doing back home. And so, after their dinner in the meadow that November night, Elizabeth Simcoe set a fire just to watch it burn.
She’d become something of a pyromaniac since she’d arrived in the colonies. Having marvelled at the thick smoke that hung like fog among the trees during a forest fire in Quebec, she’d become fascinated; her diary is filled with flames. She marvelled at everything from the static in her silk gowns to a house fire that spread through Quebec to the rumours of a volcano somewhere outside that city. And once she reached the frontier, she began to set her own fires. She found them beautiful: the bright flames and billowing smoke.
That night on the peninsula, she set fire to some long grasses. She watched as they quickly burned, the flames and smoke racing fast along the ground. She wrote about it in her diary: “It had a pleasurable effect.”
And that wasn’t the only freedom Elizabeth Simcoe was indulging out there on her secluded sandbar. She was also spending a suspicious amount of time alone with a dashing young man who was not her husband.
Elizabeth Simcoe had been married for more than a decade, having met her husband when she was a teenager. John Graves Simcoe was a daring young officer recently returned from the battlefields of the American Revolution. The British might have lost the war, but Simcoe had made quite a name for himself fighting against the revolutionaries. He’d never lost a battle, he’d survived a rebel prison, and had been wounded three times. With the war ending, he’d gone home to England to recover and heal — not just from his injuries, but from a broken heart, as well.
Just a few winters earlier, Simcoe had found himself living outside New York City. The area was controlled by the British, but there were still plenty of American rebels about. So, Simcoe spent his days on patrol with his men, 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. His daring deeds made him a hero to the British, while many Americans came to see him as a particularly vicious foe, accusing him of massacres and remembering him more than two hundred years later as a psychopathic villain in an ahistorical Netflix show.
But on some nights, things were much more peaceful. Simcoe was billeted with an American family who lived in Oyster Bay, a small community on Long Island. And it was there during those cozy winter nights that he fell in love.
Sally Sarah Townsend was eighteen years old. Simcoe was twenty-seven, a brave young officer looking for a wife. They say his fellow soldiers were deeply jealous of the flirtatious hours he got to spend with her. “She was the toast of these young men,” as one historian would later put it, “and Simcoe was regarded as a most fortunate being in basking in the daily sunshine of her charms.” By the time the fourteenth of February came around, Simcoe was thoroughly smitten.
To prove the depth of his feelings, he turned to a relatively new English tradition. People had been sending Valentine’s Day cards for centuries, but it was in the 1700s that they really evolved into the popular romantic tradition we know today. As a lover of poetry, Simcoe seems to have fully embraced the practice. And to celebrate St. Valentine’s Day in 1779, Simcoe penned an ode to Sally Sarah Townsend.
The poem began simply enough:
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!
But it quickly evolved into something much more ambitious. Thirteen stanzas and three hundred words long, Simcoe’s poem ended with a prayer to the God of Love asking whether his life would ever be more than just endless war:
“Fond Youth,” the God of Love replies,
“Your answer take from Sarah’s eyes.”
Along with the poem, Simcoe also attached a sketch: two hearts inscribed with their initials and joined together by Cupid’s arrow. Today, it’s considered to be the very first Valentine in North American history.
But no matter how strong Simcoe’s feelings were, how flattering his poetry or romantic his art, the two could never be together. He’d fallen in love with the wrong woman. Sally Townsend was a rebel spy.
With the British 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 the area. The Culper Ring was a huge success. It 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.”
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 he brought his sister on board as an informant. It’s thought that she may have been spying on Simcoe the entire time he was wooing her, her flirtations nothing more than a rebel ruse. As the daughter of a revolutionary family, she certainly had 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, using the wood to reinforce a nearby fort.
As you might expect, Townsend rejected Simcoe’s plea to take him as her Valentine. The last surviving physical trace of their relationship is a pane of glass from her bedroom window, still preserved at her old house in Oyster Bay (now open to the public as the Raynham Hall Museum). There’s a wistful message scratched into its surface — a few longing words of love thought to have been inscribed by the besotted Simcoe: to “the adorable Miss Sally Sarah Townsend.”
He wouldn’t have to live with the rejection for long; Simcoe’s days of living with the Townsends were numbered. Later that same year, he was captured in a rebel ambush and locked up inside a dank prison cell, where his health began to fail him. It was six months before he was finally released in a prisoner exchange so he could head home to England and recover. He sailed back across the ocean, armed with a fresh distrust of Americans and the democratic ideals they fought for, heading to his godfather’s quiet house in the countryside so he could lick his wounds and plan his future.
It was there, at Hembury Fort House, that John Graves Simcoe met his future wife.
It was the old admiral Samuel Graves who brought them together. He’d been war buddies with Simcoe’s dad — both were captains of ships sailing the St. Lawrence during the Seven Years’ War. Simcoe’s father had died there, catching a fatal case of pneumonia just a few months before the Battle of the Plains of Abraham. But Graves survived to become an admiral, in charge of the whole British fleet in North America during the early days of the American Revolution. It didn’t go very well; he was instructed to maintain control of the entire east coast of the United States with only about two dozen ships, an order that has gone down in history as one of the most impossible tasks ever asked of a naval officer. Admiral Graves was doomed to fail. When he was finally replaced, he headed back home to his wife and their country estate in Devon, where he would live out the rest of his days in relative peace and quiet.
The old admiral and his wife didn’t have any children of their own, but they did have a niece: Elizabeth Posthuma Gwillim.
Elizabeth had been an orphan for essentially her entire life. Her father had died during the Seven Years’ War, before she was born, having served as aide-decamp to the famous General James Wolfe on the Plains of Abraham. Her mother had died just hours after giving birth. And so, Elizabeth spent her childhood living with relatives, much of it with her uncle, Admiral Graves. She became the daughter he never had.
Hembury Fort House stood in the Blackdown Hills of Devon, one of England’s official Areas of Outstanding Natural Beauty. “Elizabeth fell in love with the beautiful Devon landscape,” her biographer, Mary Beacock Fryer, writes, “which she grew to regard as her spiritual home.” It was a land of rolling green hillsides and fields, where ancient trees lined sunken roads. It’s a land of magic and of myth, filled with tales of faeries and pixies, of warrior ghosts and witchcraft. She went for long walks and horseback rides through the hills, sketching the countryside and collecting plants. Back at home, she turned those sketches into watercolours and stayed up late reading or chatting with her best friend.
She was nineteen years old when young John Graves Simcoe arrived, a gallant warrior in his late twenties, a wounded hero with political ambitions. He made a striking impression. There’s a chance the two might have already met; they were born, by complete coincidence, just a few kilometres from each other. But even if they had, Elizabeth would now make her own new impression. She was pretty and slight, just about five feet tall. She could paint and draw and do needlework, was well read and spoke three languages.
As soon as his wounds healed, John began to join Elizabeth on her rambles through the countryside, up and down those big green hills. He, too, fell in love with the place, fascinated by its history: stories of Druids and smugglers, Bronze Age burial mounds and Stone Age earthworks. Together, they would venture up to the top of the nearest hill: an Iron Age hill fort that had once been used by the Roman army. They would make sketches of the picturesque landscape, recreating them as full paintings when they returned home. And while at first they were accompanied by the admiral’s wife — she was skeptical of the young relationship — soon, she let them go out on their own. They would stride down the old sunken roads, with Elizabeth having to run every few steps to keep up with her tall soldier.
“From walks the couple graduated to long rides each morning before breakfast,” Fryer writes in her biography. “To Mrs. Graves’ chagrin, she found herself looking on, helpless, as the two were obviously falling in love. Admiral Graves was delighted with the train of events, and sought to give the couple every encouragement.”
It worked. Just a few months after Simcoe arrived in the Blackdown Hills, the two were engaged. It was the summer of 1782. That December, they made the short trip down the hill from Hembury Fort House to a nearby church. There, they were married in front of their friends and surviving family members. With Elizabeth’s inheritance, they bought a beautiful estate of their own, just across the fields from Hembury, where they began their family.
It was almost a decade later that John Graves Simcoe was called back to North America. In the wake of the American Revolution, tens of thousands of refugees fled the United States. Many Americans who’d stayed loyal to the British during the war were forced from their homes by the revolutionaries, their lives threatened, their property burned to the ground. A wave of these Loyalists fled north to the Canadian colonies, where the British still ruled. And while the settlements of Quebec and the East Coast were already well established, the British saw the land to the west as an untamed wilderness. Dismissing the fact that many First Nations already lived around the Great Lakes (as they had for thousands of years), the British decided that the area would make a perfect new home for the refugees. And so, the province of Upper Canada was created in what’s now southern Ontario.
For a while, the British were considering William Johnson’s son to run the new province. John Johnson had taken over his father’s job as the superintendent of Indian affairs — and as Molly Brant’s stepson, he had a strong relationship with the First Nations. But in the end, the colonial rulers chose someone else: a vehement defender of all things British whose heart had once been broken by one of those dastardly American rebels. They chose John Graves Simcoe.
In 1791 he set sail for Canada. His mission was clear: to build a prosperous new colony that was British to its core and prepared for the day when war with the Americans would break out once again.
But he didn’t go alone. Elizabeth Simcoe joined him on the long journey across the Atlantic. It must have been an exciting and romantic time, spending a winter in Quebec, taking in the views from the city’s impressive stone walls: the lower town spread out below them on the banks of the vast St. Lawrence River, with the blue hills of Maine in the distance. It was a “grand scene,” she wrote in her diary, “with which we were so delighted that we came to view it again in the Evening & did not return home till it was dark or rather starlight.” She would give birth to their seventh child nine months after that romantic stroll, almost to the day.
She was pregnant during the harrowing trek up the St. Lawrence to reach their new colony, but as soon as they arrived in Upper Canada, she would get to work. She had an important role to play. While the lieutenant-governor prepared for war and planned his province, Elizabeth would be tasked with bringing the genteel culture of English drawing rooms to the dark forests and deep waters of the Canadian frontier. Together, they would build a British utopia.
As their ship dropped anchor at the entrance to Toronto Bay on that July day in 1793, John Graves Simcoe had a clear plan in mind. He would build a new capital here; protected by the sandbar, it was much safer than the old capital at Niagara, where an American fort sat just across the river. The newly reconstituted Queen’s Rangers were already hard at work clearing trees to make way for the settlement. When it was done, it would be a glorious tribute to the British Empire: a city so undeniably amazing that the Americans he’d fought during the revolution couldn’t help but realize how terrible the United States was by comparison. They would voluntarily give up their silly notions of independence and beg to be let back into the Empire.
“I would die by more than Indian torture to restore my King and his family to their just inheritance,” Simcoe wrote before he left for Canada. “This colony … should in its very foundations provide for … every embellishment that hereafter may decorate and attract notice, and may point it out to the neighbouring States as a superior, more happy, and more polished form of Government. I would not in its infancy have a hut, nor in its maturity, a palace built without this design.”
Indeed, Simcoe set to work making his new settlement as British as possible in every detail. Many of the first few streets in his new town would be named in honour of British royalty: George, Frederick, and Adelaide among them. Yonge Street would be christened in tribute to one British minister of war; Dundas to another. The river known to the Anishinaabe as Wonscotanach would be renamed after an English river: the Don. The Niwa’ah Onega’gaih’ih was already being called St. John’s River by the time the Simcoes arrived — a reference to Jean Baptiste Rousseau. But it would now be known as the Humber in honour of a river in Yorkshire. And it was Elizabeth herself who named the towering cliffs to the east of the town. They reminded her of some cliffs in Yorkshire, so she gave them the same as that place: Scarborough.
Even the word Toronto would be replaced. When Simcoe learned that King George’s son — the Duke of York — had won an important victory over the French, Simcoe announced that he would name his new town in tribute to the prince. The honour was a bit premature; the duke’s campaign against the French fizzled, and he would soon be caught up in a notorious sex scandal. His former mistress claimed she’d taken bribes in return for using her influence with him. But Simcoe couldn’t have known that any of that was coming. To celebrate his town’s new name, he ordered a Royal Salute: all the cannons on the shore, all the guns on all the ships in the harbour, all the muskets of his soldiers were fired in honour of a man who would soon be at the centre of what’s been called “the greatest scandal in the history of the British Parliament.”
Toronto would now be known as York.
This new city would also have a strict class system, much like England’s, with power kept in the hands of those at the very top. As far as Simcoe was concerned, democracy was dangerous. During the American Revolution, he’d personally witnessed horrors committed in its name, and now the idea had spread to France, where an even bloodier revolution was underway. So, he would restrict what he once called “tyrannical democracy” in favour of a powerful, British-Canadian elite.
There would be limits on personal freedom, too. Love would be strictly regulated. Marriage would play a vital role in Upper Canada, creating a strong foundation for the colony, but only if it were properly controlled. Settlers on the frontier had enjoyed too much freedom. To be a respectable British province, Simcoe wanted respectable British marriages. That meant not only a crackdown on less traditional forms of love, but also a strict definition of what constituted a “proper” marriage.
For Simcoe, that meant one thing: an Anglican marriage. In Upper Canada, there would be an official state church: the Church of England. The only valid marriages were those performed by Anglican ministers. It was one of the founding laws of the province, adopted on the very first day Simcoe’s new Parliament met.
But that limited definition of marriage caused major problems. Upper Canada was already a much more multicultural place than Simcoe wanted it to be. The majority of the settlers weren’t Anglican at all. And with only a handful of priests on the frontier, it was hard to get an Anglican wedding even if you wanted one. In one fell stroke, countless marriages had been called into question.
Simcoe had a tremendous amount of control over his new province. There was an elected Legislative Assembly, but it had little power. It could be overruled by the un-elected Legislative Council and by the lieutenant-governor himself. Still, Simcoe couldn’t just create whatever laws he wanted; he did need the assembly’s support. And even some of his own allies worried their marriages were suddenly invalid. The very first new bill introduced in Parliament sought to expand the definition of marriage. Simcoe would eventually be forced into compromise. The law was changed to allow exceptions for just a handful of other Christian denominations. But that really just caused even more confusion. The fight would carry on well into the 1800s.
In Upper Canada, for decades to come, it would be unclear who really was married — and who wasn’t.
Elizabeth Simcoe had her part to play. There, in her little canvas house on the shores of Toronto Bay, she was helping to recreate the culture of English drawing rooms. As the lieutenant-governor’s wife, she was at the centre of social life in the province. Everyone was looking to her to set the example. Even in Canada, she did all she could to keep her hair perfectly coiffed and to dress in the latest fashions. She’d brought servants with her from Europe, including a French chef and a nurse for her children. She’d even brought a spinning wheel with her — hauling it all the way to the frontier even though she never used it, just because it was a gift from the queen.
At York, as spring arrived and the first few government officials began to follow the Simcoes across the lake, Elizabeth hosted dances, dinners, and card games — staples of respectable English culture. At Niagara, she’d even hosted royalty — Prince Edward, father of Queen Victoria, had paid them a visit on the frontier. A “lady of manners” is how one acquaintance described her. “Her conduct is perfectly exemplary, and admirably conformed to that correct model, which ought to be placed before a people.”
But she was also enjoying the new freedoms she found out there on the frontier: exploring the wilderness, eating raccoon meat, painting her watercolours on birchbark, and setting her fires.
Thomas Talbot was her husband’s private secretary. He was twenty-two years old, a dashing adventurer from one of Ireland’s most storied noble families. He’d joined the army at the age of eleven, served as aidede-camp to the governor of Ireland, and become close friends with the Duke of Wellington — the general who would defeat Napoleon. It was Talbot’s military career that had brought him to Canada; he’d served in Quebec City and Montreal before heading out to the frontier with the Simcoes.
At York, Elizabeth spent a lot of time alone with the handsome young Talbot. He was much younger and more vigorous than her husband. Simcoe was not a healthy man — he’d missed Prince Edward’s visit, bedridden the entire time, and would eventually die of a severe asthma attack. Talbot was clearly in the prime of his life. When the three of them walked across the frozen bay (on the same day she set her first fire), it was Talbot who took her by the arm, while the lieutenant-governor trailed behind, treading carefully with the help of a cane. She had plenty of adventures with her husband’s secretary when her husband wasn’t around. They dined together; he frequently drove her home from events in a carriage or a sleigh. They were together when she saw her first bald eagle, soaring through the skies at Niagara. She watched, amused, as Talbot tried to paddle a canoe for the first time. And when she’d been upset by the sight of some passenger pigeons flapping and squawking, trapped in a cage, it was Talbot who paid to have them released. When he met with local Indigenous leaders, he brought gifts back for her: a berry cake and a fawn skin she made into a long shawl. Reading her diary entries, it’s easy to imagine a romance budding between the two. Out there on the peninsula, away from the eyes of her husband and the soldiers building Fort York, she and Talbot raced their horses across the sand, hooves thundering on the beaches, the cool autumn air rushing against her face.
But in the end, that’s not the life Elizabeth Simcoe chose. Her adventures in Canada were brief. She returned home to England with her husband after just a few years; his health was suffering from their rustic lifestyle. They would never return.
Thomas Talbot would remain a bachelor for the rest of his days, living on the shores of Lake Erie. He built an empire there, entrusted with a huge swath of land, which he distributed to new settlers. Eventually, it would stretch more than a half a million acres, home to fifty thousand people. You’ll still find his name written across that part of Ontario to this day: the city of St. Thomas was named after him, and London has Colonel Talbot Road.
But he kept one big chunk of land for himself: a generous patch of wilderness surrounding his home. He’d built a log house on top of a bluff overlooking the lake. He grew old there, a rich and powerful man living the simple life of a recluse. He raised sheep, cattle, and geese; grew a fruit orchard and a rose garden; and hired one servant with a wife and child. Every year, he would attend a single ball, always taking the first dance with the most beautiful young woman there. But beyond that, he was rarely seen in public.
Decades after the Simcoes left, when Talbot was in his late sixties, a famous writer came to pay him a visit. Anna Jameson was an ardent feminist who had briefly come to Toronto to get a separation from her husband, the attorney general. She leaped at the opportunity to explore the province, and her tour of Upper Canada included a visit with Talbot on his wild estate. While she was a bit scared to meet him, having heard stories of a curmudgeonly hermit who hated women, what she found instead was a welcoming old man who still remembered the charms of courtly life. “In spite of his rustic dress,” Jameson wrote in her account of her travels, “his good-humored, jovial, weather-beaten face, and the primitive simplicity, not to say rudeness, of his dwelling, he has in his features, air, and deportment, that something which stamps him gentleman … which thirty-four years of solitude has not effaced.”
She stayed with him there in his log house for nearly a week, keeping him company, listening to him talk about his life. She found that tears sometimes came to her eyes as he did. He was happy but lonely. No one knew for sure what had driven him to lead such a reclusive life. But some, Jameson wrote, whispered “that early in life he had met with a disappointment in love, which had turned his brain.” He spent the rest of his life there in that log cabin high above Lake Erie, many long years after he and Elizabeth had raced their horses along the shores of Toronto Bay, picnicked in the meadows of the peninsula, and watched her fires burn. Thomas Talbot seems to have died as he lived: a hermit with a broken heart.
As for Elizabeth Simcoe, she would spend the rest of her life in Devon, watching over her country estate. She would never again experience anything like the freedom of those fleeting days on her beloved peninsula. She would outlive her husband by nearly forty years, a widow becoming ever more conservative as she grew older. John Graves Simcoe was laid to rest beneath the chapel they’d built together in those green hills — a spot that many years later would officially be declared Canadian territory: a small patch of Ontario in the middle of the English countryside. And when Elizabeth Simcoe finally died at the age of eighty-seven, she, too, was buried there, beneath that little church, thousands of kilometres from Canada, right next to the man she’d married.