The Upper Canada Rebellion was the catalyst which led to the fighting of the Patriot War. Led by disgruntled Upper Canadians in December 1837 who wished to implement democracy and responsible government in the British colony, their failed coup led to the flight of hundreds of rebels to America. In America, the rhetoric of freeing Upper Canada from under the yoke of British oppression by installing a republican form of government, along with promises of wealth and land, enticed hundreds of Americans known as ‘Hunter Patriots’ to join forces with Canadian insurrectionists and lead multiple assaults into Upper Canada.
The Gathering Storm: Rebellion in Canada and the Road to the Patriot War
On December 7th, 1837, a large force of over 1000 fighting men could be found marching up Yonge Street in the city of Toronto, located within the British colony of Upper Canada (present-day Ontario). Their goal was a roadside inn known as Montgomery’s Tavern, which at that time was being utilized as a makeshift base for hundreds of rebels.
These rebels, in essence, sought to overthrow British rule in the colony in favor of “responsible government” and republicanism, or, put more simply, democracy. In 1837 Upper Canada was essentially ruled by the Lieutenant-Governor who would handpick members of the Executive Council branch of government. While elections were held for the House of Assembly, this was a lower level of government. Anything the democratically elected House of Assembly put forward could quickly be vetoed by the handpicked Executive Council and Lieutenant Governor, thus making the elected government branch almost entirely pointless.
The Executive Council was also known as the “Family Compact”. Even though they had no familial relations, they were all wealthy men and staunchly British who looked out for each other’s interests through corruption and by appropriating government money. Those who spoke against them, like Robert Bidwell, were often arrested and banished from Upper Canada. To speak out was treasonous and showed disloyalty to the British crown.
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Anger at the Family Compact and the Lieutenant Governor created a spark that quickly burst into flame. The common person of Upper Canada increasingly suffered under the yoke of the aristocracy, and rumblings of insurrection began to increase as the economy plummeted and the corrupt Upper Canadian government continued to appropriate taxpayer money for their own business interests.
Under the guidance of rebel William Lyon Mackenzie, a member of the House of Assembly, word began to spread throughout the province. The time was now — the rebels, also known as “radicals” and “reformers,” began to train and meet in secret throughout the province with a planned rendezvous in December of 1837 at Montgomery’s Tavern where the final assault on Toronto would be carried out.
The actual motivations of the rebels are unclear, as they certainly did not have a coherent motive. Very few wished to actually overthrow the might of the British Empire in North America, and they would have been aware of the foolishness of such a proposition. However, they were equally confident that the corrupt aristocracy and the Family Compact could no longer govern their lives, and thus an American style of government needed to be implemented.
In a tremendous stroke of fortune, the Lieutenant-Governor of Upper Canada at the time, Sir Francis Bond Head, had sent the entire contingent of British regulars to Lower Canada (modern-day Quebec) to fight a sister rebellion there. So, when the rebels finally amassed at Montgomery’s Tavern on December 4, 1837, Toronto, with all its munitions and government officials, was defended only by a militia force.
The Battle of Montgomery’s Tavern
After several days of posturing and failed marches, the rebels remained in a state of agitated paralysis at Montgomery’s Tavern due to poor leadership and being undermanned by soldiers. Many of the revolutionaries did not even carry guns, and others quickly grew disenchanted at what increasingly seemed to be a doomed venture. The strange behavior of their leaders did not help matters — for example, rebel leader William Lyon Mackenzie had taken to wearing several thick layers of coats — the reason for this, it was rumored, was to stop bullets.
Aware of the rebels’ location and of their dwindling numbers, the loyalist militia in Toronto went on the march toward Montgomery’s Tavern on December 7. Proper equipment was of no issue here — despite the lack of British regulars, the might and funds of the British Empire were behind them. Bayonets and muskets glinted in the bright sunlight, cannons rolled along imposingly, and drums beat a fearful tune as the Lieutenant-Governor Bond Head himself led the loyalist fighting force to the tavern.
The Battle of Montgomery’s Tavern was brief and decisive. After exchanging musket fire that felled a few soldiers on each side (casualties for the entire encounter were less than 15), a cannonball blasted straight through the tavern’s dining room and out the other side. For the beleaguered reformers, this was the final straw. Rebels began pouring out of the inn in full flight, seeking refuge in the forest where they could return to their peaceful lives as farmers and laborers. Some escaped, while others were captured, pardoned, exiled, or executed.
While the defeat at Montgomery’s Tavern was decisive, the saga of the Upper Canada Rebellion was far from over. At this juncture, the Americans entered the fray in a surprising twist of fate. As rebels fled into the woods, many leaders, such as William Lyon Mackenzie King, John Rolph, and Charles Duncombe, knew full well that their time in Upper Canada was up. They would now be hunted men, and flight was imperative. Many rebels, including these leaders, successfully slogged across the frigid colony into the relative security of the United States.
“The Americans Are Coming!” From Rebellion to Patriot War
There, the idea of liberating Upper Canada from under the oppression of the British Empire quickly began to take hold of certain members of the American populace who felt strongly about the need to implement American republicanism and democracy in Upper Canada. Hundreds of Americans flocked to William Lyon Mackenzie and other leaders as they promised unspecified riches and land for those who aided in completing the work the Upper Canada Rebellion had begun.
These men were known as “Hunter Patriots” and were grouped in covert “Hunters Lodges” throughout the northern United States. The motives of these new American allies were also unclear. While some were keen to provide Upper Canada with greater democracy and responsible government, others were lured only by the promise of land and riches or the draw of adventure and combat.
Nevertheless, the Upper Canada Rebellion had now morphed into the “Patriot War” as melded groups of escaped rebels from Upper Canada and American sympathizers began to lead attacks across the border. Of course, it is imperative to note that the American government wanted no part of this Patriot War and did not wish to invoke the wrath of the British Empire. Likewise, the British government desired no open hostilities with the Americans, who were quickly becoming trusted friends and trading partners after reaching diplomatic lows in the War of 1812.
Opening Encounters: The Beginning of the American Patriot War
However, the desires of high-ranking officials held no sway over these men who desired war and the “liberation” of Upper Canada from British oppression. The rebel and American forces were encamped on Navy Island, a small islet between the neighboring countries on the Niagara River. They began to plan for an attack on Upper Canada. To deter the gathering force of rebellious Canadians and eager Americans, the royalist forces were aware of the need to eliminate the Caroline to cut the supply line to the island. Colonel Sir Allan MacNab, an eminent member of the Family Compact, led a mission to ensure the ship could no longer be used to undermine British authority.
On December 29, 1837, the battle for the Caroline was swift and conclusive, as the crew was taken completely by surprise. Shots were fired, and one American crewman was killed, a man named Amos Durfee. His body was placed in front of a bar in Buffalo, New York, by “sympathizing patriots” who desired to create anger among other Americans and convince them to join their fight against the British. MacNab and his men towed the Caroline into the river and set it ablaze. Much of it sank, while other pieces tumbled over the Niagara Falls.
Despite the insignificance of the vessel itself, which was small and not militarily important, this occurrence nearly created an international conflict and became known as the “Caroline Affair.” Americans were enraged that British forces had lightly defied American authority by destroying an American ship in peacetime. At the same time, the British countered that the vessel was an agent of traitorous interests and threatened British power.
“Revenge for the Caroline!” The Americans Strike Back
Destruction of the American Caroline by the British, by L.M. Lefevre & J. Bouvier, 1838, via the National Maritime Museum, Greenwich, London
While the turmoil slowly died down with no more significant political consequences, the American desire for revenge grew among the lower ranks of society. On May 29, 1838, a large group of American “Patriots” and Upper Canadian rebels attacked the massive Upper Canadian steamship, the Sir Robert Peel, as it was docked for reprovisioning. The Peel, a striking and impressive vessel at almost 400 feet in length, was also a new addition to Upper Canadian waters, as construction was only completed in 1837. Because of its gargantuan size and importance to the colony, it became the goal for American aggressors pursuing retribution. The insurgents, led by famed pirate Captain Bill Johnson, robbed the travelers and sank the ship in the Saint Lawrence River, shouting “Revenge for the Caroline!” a nod to the loss of the American steamer earlier in the year. The destruction of the Sir Robert Peel was a substantial commercial loss for the province of Upper Canada, as voyagers were standard on its deck.
After the destruction of the Caroline and the Sir Robert Peel, the enmity between the two nations reached a breaking point as both called for apologies and reparations. Unsurprisingly, the British refused to budge, as did the Americans.
Undeterred and unconcerned by the haggling between government officials, bands of rogue Americans continued to cut a bloody swath across Upper Canada throughout 1838. Common people were attacked and robbed, and towns were raided. While compared to the War of 1812, this “Patriot War,” which stemmed from the Upper Canada Rebellion, was little more than isolated skirmishes, the simmering anger between the two nations was at risk of boiling over as more significant numbers of Americans were driven by the idea of liberating Canada from British political authority, convinced by the rogue Upper Canadian leaders.
The Battle of the Windmill
Of course, the fact that the vast majority of the people of Upper Canada remained loyal to the British crown and had no desire to implement American Republicanism was of no consequence to these Hunter Patriots. Undeterred by their small numbers, the Patriots boldly led an assault with 250 men on the Canadian town of Prescott in November 1838. The subsequent military action would be known as the “Battle of the Windmill” and the largest and bloodiest encounter of the rebellion. Taking possession of the small village of Newport on the outskirts of Prescott, the Patriots holed themselves up in an imposing windmill that overlooked the town as they awaited promised supplies and reinforcements from other Patriots still stationed in the United States. Their decision was a good one — they had not only successfully occupied Canadian soil but had also picked a highly defensible position with thick walls.
Soon after, the might of the British military descended on the sleepy village of Newport. Numbering over 500 highly trained British regulars with the aid of over 1000 Canadian militiamen, the US Navy also threw in their lot with the British to blockade the river and stop the Patriot reinforcements from joining their allies at the windmill.
Although their position was precarious in the face of a combined force of British regulars and the US Navy patrolling the river, the Patriots surprisingly decided to fight and scoffed at all ideas of surrender. The first assault on the windmill was handily beaten back by the Patriots; thanks to their fortified position and vantage point, the Patriots were able to inflict heavy casualties on both the Canadian militia and even the trained British regulars, sending them reeling with over 80 casualties on the first day.
However, the doomed nature of the situation slowly began to set in for the Patriots. Completely blockaded and surrounded, their own casualties mounted over the next three days as 110 of their original 250 were either dead or wounded. Faced with insurmountable odds, the Patriots surrendered on November 16, 1838. Those who survived were either exiled, imprisoned, or executed after trial.
A Final Gambit: The Last Stanzas of the Patriot War
Despite their losses at Prescott in November, the Patriots rallied and planned a final assault on the large Upper Canadian town of Windsor, across the border from Detroit. This attack, again led by the alliance of refugee Canadians and idealistic Americans, was the last full-scale assault by the Patriots of the campaign. However, unlike at the Battle of the Windmill, their chances of success were surprisingly high due to a surprise advantage. Windsor was defended exclusively by militia at this time, and the townsfolk had grown weary of their incompetence, negligence, and general dereliction of duty. Indeed, one irate citizen of Windsor stated that the “sentinels were placed without judgement, and their duties were performed in the most slovenly and unsoldier-like manner.” (Battle of Windsor, 1838).
Thus, with this advantage, 140 Hunter Patriots glided smoothly and silently across the river from Detroit to Windsor on the night of December 4th, 1838. Not only was the Canadian militia taken unaware, but they were also heavily outnumbered by the most significant force their enemy had fielded in the American Patriot War.
Much like at the Battle of the Windmill, the opening stages of the attack on Windsor swung decisively in favor of the American insurgents. After landing undetected on the banks of the river, the Patriots burst into the town, setting fire to several buildings and even burning the giant steamship the Thames, a ship of great economic and strategic significance to the town. The emboldened Patriots raced through Windsor, heading directly for the Upper Canadian barracks that they knew were full of arms and munitions.
Only a single sleepy sentry stood watch outside the barracks. While he was able to rouse his fellows and get them under guard, the surprise attack of the Americans quickly overwhelmed them. Within minutes the Canadian militiamen were either in full flight out of town or taken prisoner as the Americans looted, ransacked, and burned their barracks and the surrounding buildings.
One particularly cruel casualty was the murder of a black man named Mills. Hearing the commotion and stepping outside his home to investigate, Mills chastised the insurgents when he was taken prisoner and was given the choice of joining their cause or death. Mills proudly proclaimed his support for the Queen and the British Empire and was cut down.
While the initial battle for Windsor had gone the way of the American cause and the Windsor militia was in full retreat, all was not lost for the Upper Canadian cause. Several brave townsfolk took off on horseback to find militia Col. John Prince, the capable and shrewd commander who commanded the nearby Essex militia.
The “Windsor Butcher” Puts Down the Patriot War
Col. Prince acted quickly and with purpose upon hearing the news from Windsor — rallying his militia around him and any volunteer he could find, they quickly set off towards the town. However, the numbers were still against them. Prince’s force only numbered 130, while the Patriots could have had as many as 140, as they had only suffered one casualty in the initial foray.
However, the element of surprise that had been such a boon for the Americans worked equally well for the forces of the Empire. In a stroke of incredible luck, Prince’s oncoming party happened upon the raiders as they briefly resting in an orchard on their way to attack the nearby town of Sandwich. At this interval, the circumstances were reversed from the initial encounter, for the royalists had now caught their enemy in a vulnerable position.
The militia opened fire on the brigands, spurred on by Prince, killing several men and wounding many others. The shock of the attack and losing dozens of men was too great for the insurgents as they broke ranks in every direction, vacating the battlefield. Almost half of their number was taken prisoner, and the Battle of Windsor was effectively over and victory assured.
At this juncture, Col. Prince acted in a manner that would give him his moniker in America — “The Windsor Butcher.” As prisoners were rounded up, it seemed a foregone conclusion that they would be handled much like a host of other apprehended insurgents and rebels — all would have their day in court, where they would be sentenced to death, prison, or exile. Prince, however, decided that macabre frontier justice was more appropriate for those who challenged British institutions.
He ordered five rebels to be executed without trial, which his militiamen did without question. The Patriots were not only executed but often killed in a brutal and unforgiving fashion. One man was shot while he sat with a shattered leg, unable to move and causing no further risk — although this was of no consequence to “The Windsor Butcher.”
The Impact of the Upper Canada Rebellion and the Patriot War on Canadian Democracy
After this resounding defeat, the spirit had largely gone out of the Upper Canada Rebellion and its successor, the American Patriot War. The American government was set on neutrality with the British, and the American Patriots and Upper Canadian rebels who had fought to implement democracy and republicanism within the British colony were now too few and cared too little, or perhaps they just recognized the overwhelming odds against them.
Recognizing the issues that obviously existed in the colonies, the British government sent the famed Lord Durham to the Canadas, where he penned the famous Durham Report. Within the report, Lord Durham made the radical suggestion that the colonies should have further autonomy through responsible government and democracy. Although these suggestions would not be carried out for another decade, the seeds had been sown — and while their methods were questionable, this was primarily because of a ragtag group of Americans and Canadians who recognized the dangers of oppression.