Cautionary Tales: The Upper Canada Rebellion and the Freedom Convoy

Jonathan Szo

On 7 December 1837, a force of 1,200 troops marched down Yonge Street in the city of Toronto under the command of Sir Francis Bond Head, the lieutenant-governor of Upper Canada. Their destination was a wayside inn known as Montgomery’s Tavern, the meeting place for hundreds of rebels who were angered by government corruption and mismanagement under the yoke of the elite ‘Family Compact.’

Upon closer inspection, it would quickly become apparent that these troops were not professional British soldiers, but instead armed civilians who were loyal to the British crown. Due to a sister rebellion in Lower Canada, Head had ordered a complete migration of professional troops from Upper Canada to fight the insurrection in present-day Quebec, despite cautionary warnings of Adjutant General Fitzgibbon, who correctly suspected a brewing insurrection in Upper Canada. Head dismissed his concerns and ordered the province to be emptied of professional military personnel.[1] The government was in denial, believing in the steadfast loyalty of the common Upper Canadian. In a now-infamous quote, a high-ranking government official proudly stated that “not fifty people” could be found to take up arms against the British crown.[2] Meanwhile, more than 600 rebels had gathered at Montgomery’s Tavern, with new supporters joining their numbers.

The government’s immense oversight left only the militia, comprised entirely of civilians. When the call went out for loyal subjects to help stave off the rebellion, the enthusiasm was unparalleled. Within a day, more than 1,200 individuals had risen in defense of the government and had mustered in Toronto.

The rebels, led by reform politician William Lyon Mackenzie, planned to seize the city in a bloodless coup, hoping to avoid violence.[3] The reformers aspired to oust the governor and council and install responsible government, which would curb the ability of hand-picked elites to decide on policy, thought to care little for the plight of commoners. Despite rebel intentions, their disorganization resulted in delays and allowed the government to organize itself.

By midafternoon on 7 December, the militia stood in front of the makeshift rebel base of Montgomery’s Tavern. With the lieutenant-governor issuing commands on horseback, the militia, armed with glinting bayonets and cannon and spurred on by drums, stepped up ably as replacements for the British Regulars. The battle was brief. The rebels dispersed in the face of artillery fire that went directly through the tavern window and exploded out the opposite side. The tavern soon stood empty as fleeing rebels vacated the battlefield. It appeared the fighting was over, and the rebellion had been broken beyond repair. Nevertheless, Francis Bond Head decided a further show of force was merited, a display that would symbolize the victory over those who had sought to destabilize the sovereignty of the British Empire. To immortalize the event, Sir Francis told his troops to burn the tavern, a gesture he saw as symbolizing the demise of “that perfidious enemy, responsible government.”[4] Of course, it does not seem to have been of great consequence to Sir Francis that Montgomery’s Tavern was the privately-owned edifice of John Montgomery, a suspected but never proven reformer who was not even present at the time.

The Battle of Montgomery’s Tavern, Unknown artist, Canadian Military Heritage, Department of Defence. via Wikipedia.

While Montgomery’s Tavern burned, Francis Bond Head made another choice that would reverberate through Upper Canadian politics in the coming years. Understanding that the home of another suspected reformer, David Gibson, was nearby, Sir Francis dispatched several members of the militia to give the same treatment to Gibson’s house that he had administered to Montgomery’s building. Gibson was not at home, but his family was. Undeterred at his absence, the militia ushered Gibson’s wife and children out into the snow and burned their house to the ground, going out of their way to ensure every structure on the property was reduced to ashes.[5]

Sir Francis Bond Head, Lieutenant-Governor of Upper Canada. Nelson Cook, painter; C. Turner, engraver; Fred. C. Capreol, publisher. 1 September 1837. Archives of Ontario, via Wikipedia

The lieutenant-governor’s determination to burn both Montgomery’s tavern and Gibson’s home had repercussions. Despite the rebels disbanding, Head imposed punishment nonetheless. He used excessive force in a civilian context when he ordered the burning of a private home and a commercial building with little cause to do so. Head was well within his rights to track down proven rebels for their day in court, but the excessive punishment taken against untried citizens in brutal fashion was a blemish that would follow the government for decades to come, until Montgomery was finally partially reimbursed in 1873 in the amount of $3,000—not the $15,000 recommended by an impartial investigator.

Not only did the lieutenant-governor use excessive force, but he engaged in the punishment himself, rather than leaving this duty to the courts. Passing judgment without due process was an inexcusable and arguably unconstitutional action, and the reverberations from that decision would be reflected strongly by the militia of Upper Canada, who were sent forth to defend the colony against any further insurgents, and frequently acted with impunity, not unlike Lt.-Gov. Head.

As civilian losses of property and possessions mounted during the rebellion, the assembly authorized a special commission to examine various claims for losses, and it convened in early 1838.[6] In a surprising twist, many of the submitted claims were against the government itself as citizens attempted to recoup damages caused by the erratic behaviour of the militia. The conduct of the militia in its “defense” of Upper Canada was often undisciplined and delinquent, seizing, for example, the homes of citizens to use as barracks, often robbing and damaging them beyond recognition before their departure.[7] In a group petition from more than 40 individuals, one lead claimant, Edward Durham, stated that their homes were “plundered and destroyed and taken from them by those very men to whom they looked for protection, and from whom better conduct might have been expected.”[8] The commissioners rejected the claims of Durham and his fellow petitioners, as well as those of other claimants who set forth complaints against the militia or the government. In 1838, the government resolved to indemnify itself against all claims that placed responsibility on them, a dubious resolution to the events set in motion by Sir Francis Bond Head.

These events from the past speak to current issues in Canada, including Justin Trudeau’s recent activation of the Emergencies Act against the anti-vaccine protestors and their occupation of Ottawa. Much as in 1837, strong demonstrations of force can quickly become problematic if government-sanctioned force, whether it be physical or political, is perceived to be used in excess against a government’s own people. For the first time since its inception in 1988, Canada invoked the Emergencies Act in response to the perceived attack on Canadian sovereignty through the actions of the ‘Freedom Convoy.’ Opposition members decried its implementation as a misuse of power. The government undertook extraordinary measures such as freezing bank accounts, restricting access to public areas, allowing for the forceful removal of individuals in these areas, and granting police additional powers to fine and jail those who disregard the new rules.

The quandary the Trudeau government faced with the anti-vaccine mandate convoy has similarities to the predicament that Sir Francis Bond Head had with Upper Canadian reformers in 1837. The anti-vaccine convoy’s actions were viewed by the government as posing a critical threat to the security and sovereignty of the nation. Yet, excessive use of force can threaten the very sovereignty one is seeking to protect. Upper Canada’s government used force against the rebels with such blatant disregard for British constitutionalism that it directly threatened British sovereignty. Regarding current events, Prime Minister Justin Trudeau felt as justified as Sir Francis Bond Head did in responding to events that overwhelmed current laws and policing capacity and resulted in a threat to the nation’s capital. Much as in 1837, it can quickly become problematic when government-sanctioned force is perceived as excessive, whether it be physical or political, and is used against a government’s own people.

While the similarities between the events are evident, their disparities provide further context on the matter. The invocation of the Emergencies Act was difficult, subject to intense parliamentary debate and mired in controversy. Conversely, the decision to burn Montgomery’s Tavern and Gibson’s home was more capricious, as the mercurial Bond Head acted impulsively, intent only on dismantling the rebellion swiftly and brutally. Still, the issue of potential government overreach remains, and is even exacerbated, as it transcends the political spectrum when considering the modern issue. Regardless of one’s opinion on the freedom convoy or the implementation of the Emergency Act, government overreach has been proven to be a disastrous experiment historically, and such issues could have far-reaching contemporary consequences as well, whatever one’s opinion or political leaning.

Regardless of any political bickering, the opening stages of the Upper Canadian Rebellion of 1837 should serve as an admonition in discussions of government overreach, responsibility, and self-indemnity. Although we will never again see an armed militia marching up Yonge Street in defense of the British Empire, the cautionary tale of the rebellion should not be quickly forgotten.


Jonathan Szo is a MA student at the University of New Brunswick, where he is studying the Upper Canada Rebellion of 1837-38.


[1] James Fitzgibbon, An Appeal to the People of the Late Province of Upper Canada (Montreal: Lovell & Gibson,

Printers, St. Nicholas Street, 1847), 10.

[2] William Kilbourn, The Firebrand: William Lyon Mackenzie and the Rebellion in Upper Canada (Toronto:

Dundurn Press, 1956), 198.

[3] William Lyon Mackenzie, Mackenzie’s own Narrative of the Late Rebellion (Toronto: Palladium Office, York Street, 1838), 14.

[4] Francis Bond Head, The Emigrant, (London: John Murray, Albemarle Street, 1847), 185.

[5] Fitzgibbon, An Appeal to the People of the Late Province of Upper Canada, 29.

[6] “Act to authorize the appointment of Commissioners to investigate the claims of certain Inhabitants of this

Province, for losses sustained during the late unnatural rebellion,” in Journal of the House of Assembly of Upper

Canada, in the first year of the reign of Queen Victoria: being the third session of the thirteenth provincial

parliament… session 1837-8 (Toronto: Printed at the Patriot Office, 1838), 39-41.

[7] “Claim of Mary Hall” in “Report of Commissioners on Claims for Losses” (hereafter “Claims for Losses”), in

Appendix to Journal of the House of Assembly of Upper Canada, from the third day of December, 1839 to the tenth

day of February, 1840 (both days inclusive), in the third year of the Reign of Queen Victoria, being the fifth session

of the thirteenth provincial Parliament. Session 1839-1840 (hereafter Appendix, 1839-1840), Vol. 1 (Toronto: W.J.

Coates, 1840), 520-521.

[8] “Claim of E. Durham,” in “Claims for Losses,” in Appendix, 1839-1840, 521-522.


Featured image: Battle of Montgomery’s Tavern, Charles William Jefferys, 1869-1952, via Wikimedia Commons.

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