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!