Battle of Windsor

By John C. Carter

Battle of Windsor: An 1838 Armed Incursion into Upper Canada, Which Resulted in Transportation to the Penal Colony of Van Diemen’s Land

Events in the Western District:

In the winter and spring of 1838, a series of armed attacks occurred in the Western District of Upper Canada along the Detroit River, and on Pelee Island in Lake Erie, and also in the summer of 1838 along the St. Clair River. Throughout 1838, residents of the Western District of Upper Canada (today’s Essex, Kent and Lambton Counties), experienced 9 attempts by the Patriot Army to “liberate” Upper Canada from British rule, overthrow the Canadian government, and establish a republican style of government.

After the St. Clair Raids (4 incursions into Upper Canada from the State of Michigan) in late June of 1838, no further violations of the United States Neutrality Act took place in the Western District of Upper Canada for nearly six months.  However, tensions continued to build in this quarter.  Robert Marsh, a Patriot who had been involved at the Battle of Pelee Island on March 3, returned to Detroit in the summer of 1838. He described the prevailing mood there; “Great preparations were being made all over the country for renewing the war.  As many of our citizens were confined, and executions taking place in different parts of Canada…and taunts and threats by tories were daily occurances, it was concluded best by many from Canada as well as thousands on this side to make one more trial.” British traveller and author T.R. Preston, recorded his thoughts about what was to come; “Under the plausible pretext of regeneration of Canada, it was apparent that an indiscriminate plunder of Canadians was contemplated.” Scottish writer Patrick Matthew also reflected on the situation, in the fall of 1838; “The late disturbances have tended much to aggravate the misery; emigration and the foreign supply of dollars has ceased, property has been destroyed, the price of foreign supplies increased, the security of property has been lessened, industry has been checked, and even though the disturbances have been put down for the present, an anticipation of future mischief continues to prevail.” A portent of what was yet to come!

The Battle of Windsor:

While mid-October rumours of a planned attack on Fort Malden [Amherstburg] proved to be false, accurate reports of Patriot forces training near Fort Gratiot [now Port Huron, Michigan] resulted in the Essex militia being called out.  An October 30 Letter to the Editor, which was published in the November 17, 1838 edition of Mackenzie’s Gazette, further described the situation; “All the Western and London Districts are in a bustle; 500 Militia are called out at Chatham; 350 are at Port Sarnia. The Militia here [Sandwich] and at Amherstburg are ordered to be in readiness at a minutes warning. The Lake Shore Militia are ordered out, and the whole of the troops at Amherstburg [Fort Malden] have been working day and night and all last Saturday getting the fortifications ready.”

[A portion of the 1836 James Farmer map of the Michigan Territory, showing the “seat of the Patriot War” in the Western District. It pin points where armed incursions took place in the spring and winter of 1838. Credit: Special Collections & University Archives, Grand Valley State University, Allendale, Michigan.]

Diligent patrols by the Detroit based Brady Guards thwarted Patriot attempts to hijack steamers on November 30 and on December 1.  A letter sent to American General Hugh Brady by local Upper Canadian magistrate Colonel John Prince on December 1, noted the urgent situation at hand; “I have ascertained from unquestionable authority that upwards of 1000 men left Buffalo a few days back in Steamers, and that they were to be reinforced all along the Shore of Lake Erie until they mustered about 5000 men; and that their determination is to make a descent upon Malden [Amherstburg] or some part of the frontier tonight. I have also this very afternoon been informed by one professing to be (but not being in reality) a ‘Patriot,’ that there is a camp no less than 400 of these Scoundrels in the woods about 2 miles back of Springwells [Michigan]; and that their fixed determination is to attack us here [Amherstburg] or at Windsor this night.” Ensign Alexander Cunningham Robertson of the 34th Regiment of Foot, confirmed this threat in his diary account entry of December 4, 1838; “For more than a month we have been kept in a state of constant readiness by the demonstration of a body of about 500 Brigands who were distributed along the Michigan frontier and threatened to invade our territory.” Robertson and the loyalist forces would not have to wait much longer to clash with the enemy!

[An 1838 view of Detroit from the Canadian side, in a period painting by Lieutenant Philip Bainbrigge. Credit: Bentley Historical Library, University of Michigan.]

Further evidence of impending trouble came from an anonymous Patriot supporter, who wrote a letter to William Lyon Mackenzie from Detroit on December 3. He noted that he had taken passage on the steamer Columbus at Clevelandwith 125 other men, landed at Toledo, and then moved on to Swan, Michigan. Here he found 300 more Patriots assembled. The group then marched to Detroit. He said that; “About 500 of us were in and around the city [Detroit], and we have been boarded at Taverns, and kept as quiet as we could.” He added that ten miles from Monroe, there were 800 more Patriots encamped in the woods at Newport. These observations all pointed to impending troubles ahead!

[William Asa Raymond’s circa 1837 graphite pencil sketch of the Port of Detroit. Credit: Detroit Institute of Arts, Detroit, Michigan]

With word received at Sandwich [now the City of Windsor] that an invasion was imminent, defending forces were put on alert.  The attack did not immediately materialize as drifting ice apparently frustrated this attempt.  The following evening Patriot General Lucius Verus Bierce and his followers marched through the streets of Detroit, and took possession of the steamer Champlain.  The rebel party crossed into Canadian waters early on the morning of December 4, landing opposite the lower end of Belle Island.  The invasion force made up of some Canadian insurgents but mostly American confederates, was estimated to number between 150-180 men. The Patriot invaders had expected that their numbers would be augmented by 500 additional sympathizers. This hoped for support didn’t come to fruition.  Patriot Samuel Snow recorded his abject disappointment; “Not a Canadian met us on our arrival save a few who joined us in Michigan, and some of these turned traitor soon after.”

The rebel forces came upon a guardhouse occupied by members of the Essex militia.  After a “short but spirited resistance” by the Canadian defenders, the position was captured and the building was burnt.  Nearby at Van Allen’s wharf, the Canadian steamer Thames was torched.  A company of Patriots commanded by General William Putnam, advanced down Sandwich Street and encamped in an orchard behind the Francois Baby house. By 6 a.m. Windsor was in the hands of the invading rebels. An alarm was raised and the Essex militia responded. At 6:30 a.m. this force engaged the Patriots. A “skirmishing fight” ensued.  Surprisingly and unexplainably, Patriot General Bierce did not attempt to assist his compatriots, nor could he be persuaded to advance to the aid of General Putnam’s besieged detachment.   Rebel reinforcements tried to cross the Detroit River to join the fray. They were challenged by American federal troops patrolling aboard the steamer Erie,and were turned back.

[J.C.H. Forster’s depiction of the storming of barracks by Patriot forces at the beginning of the Battle of Windsor. Credit: Fort Malden, NHSC, Parks Canada]

Enthusiasm for the invasion into Upper Canada was evidenced in Detroit.  Thousands of residents assembled along the river front to vocally show their support for the fortunes of the Patriot forces. Patriot Robert Marsh recorded the spectacle that he witnessed across the river from Sandwich; “There were thousands to be seen at day-light, on the tops of buildings swinging their hats and cheering us on our morning’s success.” Without any additional armed support, General Putnam was compelled to order his forces to withdraw. Upper Canadian Patriot Elijah C. Woodman provided an on the spot rebel perspective of the defeat; “After a sharp fight we drove them back towards Sandwich but they were reinforced by the 32nd Regiment of Regulars under command of Col. [John] Maitland. This combined force was too much for us and we were repulsed and driven back to the river.”

Henry Grant, the editor of the Sandwich Western Herald and a member of the militia involved in the action, described the scene that he witnessed; “The straggling volunteers of Sandwich, of whom we had the honor to constitute a part, came up in time to send a few leaden messengers after the fast-footed pirates, who fled with a velocity unexampled in the annals of locomotion.” Private T. Rose of the 34th Regiment, provided further on the spot observations of what he saw; “How the rebels did run when they saw us come. The poor devils dropped like cocks – when we gave them steel they ran into the woods where most of them were taken prisoner.” The Patriots were caught in a murderous cross-fire, and 26 men including General Putnam were killed.  Pandemonium reigned supreme as the rebels attempted to escape.

On December 6, American Brigadier General Hugh Brady wrote from Detroit to his superior General Rogers Jones. In this correspondence, Brady provided his own personal account of the Battle of Windsor, saying that; “…about 240 of these misguided men, effected a landing upon the Canada Shore nearly opposite this City, about 4 o-clock on Tuesday morning, surprised a small guard burnt the building occupied as barracks, & a Steam Boat lying at the wharf.  After a slight action, between them and a few Militia hastily assembled, the Patriots gave way, leaving 17 killed, with the loss of but four on the part of the Loyalists. On arrival of a reinforcement of regular troops from [Fort] Malden, the Patriots broke & took to the woods, with the exception of some forty who escaped in canoes to Hog Island [Michigan].”

By 8 a.m., the Patriots had been routed. Colonel John Prince sent the militia back to Sandwich to counter another rumoured attack.  Initially 25 Patriots were taken captive.  Prince ordered that 5 prisoners were to be summarily executed on the spot.  Other escapees were arrested by American troops patrolling the Detroit River.  The remainder of the invading force was tracked down by Indians and British regulars, and those captured were incarcerated in the Sandwich Gaol.  In his December 7, 1838 diary entry, Lieutenant Henry Rudyerd, Staff Adjutant for the Western District and a close friend of Colonel John Prince, wrote of the Battle of Windsor; “…an affair had happened there, a landing having been made by the Brigands at Windsor and after burning a house occupied by the Volunteers as a Barrack & the Steamer Thames, met by the Militia and completely routed a number having been killed & taken prisoners.” Lieutenant Charles Parker also later recorded the specifics of these events in his diary; “The rebels were met by Colonel Prince who utterly defeated them killing 25 of them and taking several prisoners, the British loss in this affair was very trifling, the defeated Brigands fled to the woods, where they perished miserably from the Severity of the Season, Numbers being found by the troops sent out after them frozen to death around fires. Fit retribution for Such lawless spirits.”

[Miniature painting of Colonel John Prince, circa 1830. Credit: Mrs. H. Henchel & Museum Windsor.]

Loyalist soldier Private T. Rose, who was engaged with the 34th Regiment in the fray, concluded; “We and the militia shot a great many of them, they were lying about the streets like dead dogs – There are a great many more prisoners wounded which we left at Windsor. The Indians and a company of ours are in the woods after the remainder.” Eventually 44 prisoners were rounded up and sent to London, Upper Canada for trial by court martial. 

Colonel John Prince’s diary account of December 4, 1838, provided brief but chilling details of the Battle of Windsor; “Awoke at 6 a.m. by an alarm gun at Sandwich. Rose & saw a fire at Windsor. Proceeded there with the Militia & found it in possession of Brigands and Pirates.  We attacked them & killed 27 and took 20 Prisoners. I ordered the first 5 taken to be shot.” A further entry in Alexander Robertson’s diary of December 4 commented upon seeing a dead man lying on the street in Sandwich, and made a direct criticism about Prince’s actions; “Enquired who he was – Was told it was our prisoner shot like a dog by order of Colonel Prince. 4 or 5 people had already been served the same way by him [Prince] and there is a great difference of opinion as to the morality of this proceeding. Right or wrong, I think the voluntary assumption of the officer of executioner did not say much for the task of the gallant lawyer.”

[Battle of Windsor Mural, at the corner of Sandwich and Mill Streets, Windsor, showing the execution of one of the Patriot prisoners after his capture. Credit: Melissa Phillips, Museum Windsor]

While the controversy over Prince’s summary executions was yet to be formally judged, and captured rebels faced trials, imprisonment, and then transportation to Van Diemen’s Land, the Patriot Army had for all intense and purposes been roundly defeated and dispersed. The Battle of Windsor was the final incursion of the 1838 Upper Canadian Rebellion.  The curtain had fallen on the “last grand act” of the Patriot War. In the aftermath, 17 men captured at the Battle of Windsor and 1 captured at the St. Clair Raids, would be found guilty for their transgressions.  The Upper Canadian Lieutenant-Governor Sir George Arthur would eventually send them with one-way tickets to Van Diemen’s Land.  There these Patriot exiles would serve out their sentences as political prisoners along with others captured at the Short Hills incursion and the Battle of the Windmill.

One year after the Battle of Windsor, and editorial in the Sandwich Western Herald assessed the existing state of affairs.  Editor Henry Grant wrote that; “We heartily trust that a continuation of the peace at present so happily existing along our borders will make ‘our folk’ forget that anything so dreadful as the ‘Battle of Windsor’ ever happened at all!”  General Hugh Brady, in November 4, 1839 correspondence with General Winfield Scott, provided an American perspective; “As far as I can learn, and I have made every enquiry, there is not the least preparation making by the Patriots on our side of the line, indeed, the frontier has not been so tranquil for the past two years, as at present, and a communication that I received a few days since from Lieut Col Airy (sic), Commanding at Malden, shows that he entertains the same opinion.” Colchester, U.C. Postmaster and Justice of the Peace John G. Buchanan, expressed similar sentiments in his diary; “The Rebells (sic) returned again in the fall of 38 & gave some trouble in Windsor when they were routed and some after the Battle were shot down by Col. Prince’s orders and were not troubled any more.”


The successful repulse and eventual defeat of invading Patriot armies at both the Battle of the Windmill and the Battle of Windsor would thankfully bring this border war to a timely close. While constituting the end of one chapter in this intriguing story, it would begin another episode which would directly link the history of Ontario with that of Tasmania. Eventually at total of 150 North American political prisoners would be sent to penal colonies in Australia. Because of these events and their aftermaths, the twinned heritage of Canada and Australia would be forever forged!

[Note: Visit the Francois Baby House Museum on Pitt Street in Windsor, and Fort Malden National Historic Site in Amherstburg, to view exhibits about the Patriot War, and the Battle of Windsor.]

Dr. John C. Carter is a frequent contributor to The Wayback Times, and he can be contacted at 

4 Replies to “Battle of Windsor”

  1. Brian Rieusset, Hobart Tasmania says:

    Many thanks John for this well researched and written story of that brief Battle for Windsor, including the distressing details of Colonel Prince’s poignant and appalling execution of five ‘prisoners of war’ upon capture, albeit that they were invaders.

  2. Deke Richards says:

    These are great articles by Dr. John Carter on the Upper Canadian Rebels! These battles are referred to in my documentary on the Canadian Patriot Prisoner exiles sent to Australia called LAND OF A THOUSAND SORROWS REVISITED.

  3. Michael Turton says:

    Great job by Dr. John Carter in describing such a fascinating chapter in Windsor-Essex County history. Although I was aware of the Battle of Windsor in the broad sense, reading about it in such detail wasn’t just educational; it was also quite compelling. The quotes cited brought the piece too life, making it very real for the reader. I hope Dr. Carter will now write about the Battle of Pelee Island, one of my favourite Essex County locales. If he hasn’t already!

    Michael Turton
    Cold Spring, New York
    and formerly of Oldcastle and Windsor, Ontario

  4. Bruce D. Aikin says:

    John’s article is very interesting. As a modern American I find two things disturbing about the description of this unfortunate incident. The first is Colonel John Prince’s summary execution of five prisoners. Was there ever an inquiry into his conduct? The second is Lt. Charles Parker’s attitude about his own forces. He says, “the British loss in this affair was very trifling.” Why was his attitude so callous about Loyalist troops?
    There is a fallacy called “presentism.” It says that we cannot judge the past by our standards. I would say that it applies in this situation.
    I wonder how Col. Prince and Lt. Parker felt when they read the report of the Earl of Durham about the Upper and Lower Canada rebellions?
    “It certainly appeared too much as if the rebellion had been purposely invited by the Government, and the unfortunate men who took part in it deliberately drawn into a trap by those who subsequently inflicted so severe a punishment on them for their error. It seemed, too, as if the dominant party made use the occasion afforded it by the real guilt of a few desperate and imprudent men in order to persecute or disable the whole body of their political opponents.” (From The Patriot War Along The New York-Canada Border: Raiders and Rebels, by Shaun J. McLaughlin, The History Press, 2012; page 182.)

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