The American General Who Died Attacking Toronto
Plus the Festival of Bizarre Toronto History draws near, the fires that ravaged the city, and more...
It was 211 years ago this weekend that the Americans invaded Toronto during the War of 1812 — still the muddy little town of York back then. So, I thought this would be a good time to share a chapter from The Toronto Book of Love (lightly edited so makes it sense by itsef) all about the American brigadier general who died trying to conquer our city…
On the last night of his life, Zebulon Pike sat aboard a warship anchored off the coast of Toronto. The USS Madison rolled gently in the waves along with the rest of the American fleet: fourteen ships carrying nearly two thousand soldiers. They waited patiently there in the dark, biding their time in the waters just south of the sandy peninsula that would eventually become the Toronto islands. In the morning, they would attack York.
The Americans were desperate for a victory. The first few months of the War of 1812 had been a disaster for them. They’d failed to gain a foothold on Canadian soil before winter set in. Now, as spring arrived and the waterways thawed, they needed a quick win to boost morale. York seemed like a perfect target. It was tiny, isolated, and much less well-defended than the city of Kingston, but it still held symbolic value as the capital. And at the foot of Bay Street, York’s shipwrights were hard at work building a sloop of war. When it was done, HMS Sir Isaac Brock would be one of the most powerful warships ever to sail the Great Lakes. If the Americans could seize it and finish it themselves, they could control Lake Ontario and secure access to the St. Lawrence. If all went according to plan, they could sail downriver and besiege Montreal. Victory at York might eventually lead to victory in the entire war.
And so, on an April day in 1813, the American fleet sailed across Lake Ontario. They were spotted at dusk; a lookout perched atop the Scarborough Bluffs sounded the alarm. That night, York was alive with activity: cannons roared in warning as townspeople braced for the impending invasion — some rushing to evacuate the town, others grabbing their muskets. Every man between the ages of sixteen and sixty was expected to defend the town.
Meanwhile, out there in the darkness, the American fleet waited. And Zebulon Pike sat down to write his last love letter…
Her name was Clarissa Harlowe Brown. He called her Clara and she called him Montgomery. She was his cousin; tall, with dark hair, and so serious that she seemed older than her eighteen years, always wearing black. She was well educated, wrote her diary in French, and would collect an impressive library over the course of her life, filling it with books in three languages.
But there was a problem when the young cousins fell in love. Clara’s father opposed the match and refused to give them permission to get married. It wasn’t, as you might imagine, because Zebulon was his nephew and the young lovers were related. Instead, it was Pike’s profession that Captain Brown didn’t like. He was a military man himself, a veteran of the American Revolution, and he knew what kind of sacrifices the wife of a soldier was forced to make. It wasn’t the life he wanted for his daughter. He refused to give the couple his blessing.
But that didn’t stop them. Zebulon and Clara eloped, sneaking away to Cincinnati where they tied the knot. Her father was furious; he forbade his nephew-turned-son-in-law from ever stepping foot on his property again.
He was right to be worried. The couple’s life together was hard. Clara didn’t like living in a military fort surrounded by soldiers. And her husband was away for long periods of time. He would become known as one of the great American explorers, sent off to map the West. One of the most famous mountains in the United States is named after him. “Pikes Peak” replaced the ancient Ute name for the mountain where their history says they were created: Tava. Today, it’s nicknamed “America’s Mountain.”
Things only got harder for the Pikes when the War of 1812 began. Zebulon was called off to join the fight, spending the war’s first summer training troops on Staten Island and then a miserable winter running out of supplies in Plattsburg. He was finally called into action as spring drew near. Promoted to the rank of brigadier general, he led his men on a gruelling winter march north to Lake Ontario, struggling through three feet of snow. One of his men was killed by the cold; several lost limbs to frostbite. It was only a month later that they boarded their ships, bound for York. “If we go into Canada,” Pike had written to his brother, “you will hear of my fame or of my death.”
As dawn broke above the shores of Lake Ontario, the attack began. The American warships sailed around the peninsula — but stopped short of trying to sneak past Fort York into the bay. Instead, they dropped anchor outside the harbour, not far from where the Exhibition grounds are today. From there, they would launch their invasion.
The leader of the operation was supposed to be an American general called Henry Dearborn. But when the time came, the old general found he was too seasick to lead the attack. So, he stayed behind while his men climbed into small, flat-bottomed boats to be lowered over the sides of the great warships.
As the Americans rowed toward shore, the defenders of York opened fire. Musket balls sizzled through the air. Mississauga and Ojibwe warriors fired from the edge of the forest and were quickly joined by professional British soldiers in their bright red coats. It was there on the shores of Humber Bay that the Battle of York claimed its first lives: dozens lay dead and bleeding as the invaders returned fire, struggling to row ashore and then clamber up the steep banks toward the men hidden among the trees. The great guns of the American warships pounded away at the shore. Fragments of skeletons would be found in that soil for at least a century to come.
Brigadier General Pike watched from the Madison but couldn’t just stand by while his men risked their lives. “By God, I can’t stay here any longer,” he told one of his staff. “Come, jump into the boat.” And with that, Pike rowed in to join the battle and take over command of the attack. It would prove to be a fatal decision.
It was hard fighting, but the defenders were badly outnumbered. Bit by bit, Pike and his Americans pushed them back, securing a beachhead. From there, they began to advance onward into the trees as a marching band played “Yankee Doodle.” American sharpshooters led the way, their green coats blending into the trees. They advanced slowly over the soggy ground and melting snow, using fallen logs as cover as they picked off the defenders one by one.
Hours passed before they finally emerged from the forest at the ruins of an old French trading post, Fort Rouillé. There, a defensive battery was waiting for them, armed with artillery. It opened fire, grapeshot hurtling through the air toward them. Pike ordered his buglers to sound the advance and the Americans rushed forward as their ships bombarded the battery.
Before the Americans could reach it, the battery exploded. A British soldier had accidentally dropped a lit fuse into a pile of ammunition cartridges. The blast ripped the battery apart, knocked out one of its guns, and killed ten of its defenders. The rest had no choice but to retreat, scrambling back across the open ground into the relative safety of Fort York.
Zebulon Pike waited. It was now a little after noon. With the warships pounding away at the fort and the defenders all withdrawn from the field, he assumed the battle was coming to an end. He ordered his men to halt within striking distance of the fort and lie down while they waited for a white flag to appear.
Pike had only minutes left to live. He took a seat on a tree stump, spending his final moments questioning a prisoner while he waited for Fort York to surrender.
That’s when it happened.
The ground shook and a great roar split the air, so loud it could be heard all the way across the lake in Niagara. There was a flash and a shockwave that raced out from the fort, hurling the American soldiers backwards — some soaring twenty metres through the air. It burst lungs and tore through intestines. A great shower of debris — stone, wood, and metal — was thrown high into the air before it came racing back toward the ground in a deadly hail. It tore through skin and crushed bone. Dozens of American soldiers lay dead. Hundreds were wounded. The great magazine of Fort York, storing tens of thousands of pounds of gunpowder, cannonballs, and musket rounds, had exploded. The blast was one of the biggest in the entire history of North America.
The British general had ordered the destruction of the grand magazine as his soldiers abandoned the fort, not wanting the ammunition and supplies to fall into American hands. The explosion must have been bigger than even he imagined it would be. Some of his own men were killed in the blast. But the full force was directed toward the attacking Americans.
Zebulon Pike was right in its path. As the smoke cleared, he was found lying on the ground, crushed by a boulder with his ribs caved in. There are a few different versions of what happened then. Some say he was carried back to his ship to die, some that he spent his final moments with his head resting on a bloody Union Jack. Others suggested that he used his final breath to urge his men to victory: “Push on, my brave fellows, and avenge your general!”
The Americans were furious. They’d won the battle. Fort York lay in ruins; the Stars and Stripes now flew above the wreckage. But the British soldiers were retreating to Kingston instead of staying behind to be taken prisoner. A column of black smoke was rising from the horizon as HMS Sir Isaac Brock was burned rather than being allowed to fall into their hands. And their beloved brigadier general had been killed. As far as the invaders were concerned, the explosion of the magazine had been a war crime.
And so now they would sack York. The two sides had reached an agreement for the surrender of the town: the Americans could ransack as much public property as they wanted, but private property was to be protected. That was something Pike had already told his men before the attack began. “The poor Canadians have been forced into this war,” he wrote in his orders, “and their property should be held sacred.” Those who disobeyed, they were told, would be shot.
But now, there was no holding them back. General Dearborn dragged his feet when it came time to sign the articles of capitulation, allowing his soldiers to run riot through the town. For nearly a week, they looted and pillaged homes and public buildings alike. They burned the Parliament buildings and the lieutenant-governor’s residence to the ground.
With the British soldiers having abandoned the town to its fate, it was up to York’s own residents to save it. Some local leaders stayed behind, risking their own lives to protect what they could. Reverend John Strachan, in particular, would be remembered as a hero for his actions that week. He badgered General Dearborn into signing the surrender, tended to wounded soldiers, and nearly got shot when he confronted some of the marauding looters himself. They say that when the Americans returned a few months later, Strachan gave them such a talking to that they agreed to return the library books they’d stolen the first time. The stories helped to cement his position as a leader of the Family Compact, the conservative clique that ruled the colony.
After six days of destruction, the American fleet finally sailed out of Toronto Bay, leaving the battered capital in peace. The ships were weighed down with treasure as they left. The invading soldiers had stolen everything they could get their hands on: money, silver, furniture, food, booze, tobacco, even the town’s fire engine and the horse that went with it. But there was more than just booty on board. One of those ships was carrying Zebulon Pike’s last love letter.
The night before the battle, once he’d finished writing, Zebulon Pike had handed his letter to his aide. “Should I fall and you survive,” he told him, “hand this yourself to Mrs. Pike.” And so, Clara was given the heartbreaking message she’d long been dreading, the one her father must have worried about all those years ago when he tried to save her from the life of an army wife:
My Dear Clara, — we are now standing on and off the harbor of York, which we will attack at daylight in the morning: I shall dedicate these last moments to you, my love, and to-morrow throw all other ideas but my country to the winds.... I have no new injunction, no new charge to give you, nor no new idea to communicate; yet we love to commune with those we love, more especially when we conceive it may be the last time in this world. Should I fall, defend my memory, and only believe, had I lived, I would have aspired to deeds worthy of your husband. — Remember me, with a father’s love — a father’s care, to our dear daughter; and believe me to be, with the warmest sentiments of love and friendship,
Your MONTGOMERY.
The Toronto Book of Love is available from all the usual places, including your favourite local bookstore and directly from my publisher right here.
Two More Tours Added to the Festival of Bizarre Toronto History!
The Festival of Bizarre Toronto History is now just a week away! As I write this, I’m just putting the finishing touches on the full schedule. And I’m incredibly excited by all the wonderful storytellers who’ve agreed to be part of it this year. I’ve still got a couple of events left to lock down, but this week I get announce two walking tours from two of my favourite tour guides in the city. You’ll find all the info below and more information at www.bizarretoronto.com.
A Very Sticky Tour of Queen West
A guerrilla art movement has been playing out on the streets of Toronto for decades — with Queen West as one of its central galleries. We'll spend Saturday evening exploring the city's sticker art scene and its little-known history with tour guide and stickerer Alex Sein.
— Saturday, May 11 at 5:30pm —
A Gross & Gory Tour of Old Toronto
We'll close the festival by diving into some of the most stomach-churning stories our city has to offer. From puddles of filth to morbid mourning traditions, the history of Toronto is filled with gross and gory tales that are hard to believe people ever thought were normal.
The tour will be led by Jason Kucherawy, owner of Tour Guys — Canada's leading walking tour company — and president of the Tourist Guide Association of Toronto.
— Sunday, May 12 at 4:30pm —
Even if you can’t attend the festival, you can still support my work. The Toronto History Weekly needs your help! The number of paid subscriptions is verrrry slowwwwly creeping up, but since this newsletter involves a ton of work every week, it’s only by growing the number of paid subscriptions that I’ll be able to continue doing it. Thank you so, so much to everyone who already has — and if you’d to make the switch yourself, you can do it by clicking right here:
The Great Fires That Ravaged Toronto
April is a blustery month in Toronto — so, maybe it’s not a coincidence that this month marks the anniversary of the two biggest fires in our city’s history. Spring winds, after all, helped spread the flames. The Great Fire of 1849 broke out 175 years ago, sweeping along King Street East — the heart of Toronto back then. Half a century later, the Great Fire of 1904 claimed a hundred buildings in what’s now the financial district. It was the worst fire the city has ever suffered.
I decided to share the story of those two fires — and the unusual circumstances behind the single death each caused — on this week’s Weird Toronto History radio segment.
It airs every Tuesday afternoon at 3:20pm on Newstalk 1010.
QUICK LINKS
The best of everything else that’s new in Toronto’s past…
HIDDEN CREEK NEWS — The City is looking into the possibility of bringing some of Toronto’s buried waterways back to the surface. Staff will report to council about it later this year. Lane Harrison writes about the idea for the CBC. Read more.
ANGRY BUTCHER NEWS — The City of Toronto Archives shared an impressive artifact on Twitter this week: a ten-foot-long petition from 175 years ago: “a request to the City to allow butchers to open their own shops, and end the St. Lawrence Market's near-monopoly on selling meat.” Check it out.
SECRET PASSAGEWAY NEWS — Jack Landau finds an easily-missed piece of Parkdale history: a bricked-up staircase that stands as “the sole remnant of a long-lost train station once used by daily commuters, and even by royalty at one point.” Read more.
BOVINE BASEBALL NEWS — I’ve been sharing a lot about the Black Bull recently. And here’s another tidbit thanks to Hogtown 101 on Twitter. The bar used have its own baseball team that squared off against the Cameron House every year.
(Click to read on Twitter.)
TORONTO HISTORY EVENTS
JANE’S WALK TORONTO
May 3 to 5 — Various times — Various locations
“Jane’s Walk is an annual festival of free, community-led walking conversations inspired by Jane Jacobs—a journalist, author, theorist, activist, and proud Torontonian. On the first weekend of May every year, Jane’s Walk festivals take place in hundreds of cities around the world. Jane’s Walks encourage people to share stories about their neighbourhoods, discover unseen aspects of their communities, and use walking as a way to connect with their neighbours.”
Free!
OLD CHINATOWN WALKING TOUR: PERSEVERANCE AND ACTIVISM
May 11 — 11am — Northeast corner of Yonge & Adelaide — Mackenzie House
“Led by the staff of Mackenzie House Museum, this walk considers the early settlement patterns of the Chinese community in Toronto. Specific focus will be given to Old Chinatown, located in Toronto's Ward neighbourhood. We will acknowledge unshared histories of Chinese individuals and communities while celebrating Asian Heritage month.”
Free with registration — suggested donation of $5.
THE BEACHES: NEW FINDINGS ABOUT AN OLD NEIGHBOURHOOD
May 16 — 7:30pm — Montgomery’s Inn — Etobicoke Historical Society
“The Beaches (not the Beach) is one of the city’s best-known neighbourhoods, and its history has been recounted in several excellent local publications. But over the course of researching and writing his new book on the history of the neighbourhood, Richard White found plenty of history – both facts and interpretations – that had not yet been told. Richard will highlight some of the key findings in his book.”
Free for members; annual memberships are $25
DOORS OPEN TORONTO
May 25 & 26 — 10am to 5pm — Various locations
“Each May, Doors Open Toronto invites the public to explore the city’s most-loved buildings and sites, free of charge. The event provides rare access to buildings not usually open to the public and free access to sites that would usually charge an admission fee. Since its inception in 2000, it has attracted more than two million visits to nearly 700 unique locations and remains the largest event of its kind in Canada.”
And this year, I’m curating the guided walks portion of the festival!
Free!
TORONTO GONE WILD
Until August 3 — Wednesday to Sunday from 12pm to 4pm — Museum of Toronto
“Toronto Gone Wild explores the city as a multi-layered habitat — starring the animals, plants, and insects that call Toronto home. Venture through different Torontonian terrains from city streets to burrows, hives, and nests, all seamlessly woven together in our downtown exhibition space. You’ll emerge with a renewed appreciation for the interconnectedness of life in the city.”
Free!
Interesting that you make no reference to Tito Le Lievre who was in the magazine at Fort York and detonated the powder magazine that killed General Pike and torched the HMS Brock. I learned this when an author Ron Shaw (lives in Perth Ontario was writing a book about Frances Tito Lelievre 1755-1830 "Tales of the Hare". First in the French Navy he changed to support the English and became a Newfoundland Regiment and participated in many battles on Lake ONTARIO. Tito was my cousins ancestor. A great read on history of Toronto too!