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Mass Escape From Fort Henry

Patriot Chronicles: The Mass Escape From Fort Henry, Some Personal Reflections

It had never happened previously, nor did it ever happen again! The mass escape of state prisoners on July 29, 1838 was a singular event in the history of Fort Henry, but it was an important chapter in the history of the Patriot Wars. Several of those involved have left personal recollections of these events and some of these specific details are recounted in this article.

After the defeat of Mackenzie’s rebel forces at Montgomery’s Tavern early in December of 1837, many of the captured insurrectionists were incarcerated in the Toronto jail. This however would not be their final destination. The jail in Toronto was overcrowded with an influx of rebel prisoners. It became necessary to transfer some to other destinations. At Kingston the common jail was inadequate to accommodate all prisoners sent there from Toronto. As a consequence, Fort Henry became a centre for the receipt of these prisoners. Several of the fort’s casements were modified and made into prison cells to house these men. In an April 21, 1838 missive written by retired diplomat Aaron Vail, he reported to John Forsyth, U.S. Secretary of State, about American citizens incarcerated in Canadian jails.

Vail provided the following description of the prisoners’ quarters at Fort Henry: “The room is twenty feet by forty, with two windows and a door opening upon the parade, which appeared to me sufficient for all purposes of light and ventilation. It was kept warm and dry by a stove; and prisoners had their beds spread upon platforms erected for the purpose.”

After trials in Toronto in May of 1838, on June 2, 15 Canadian Patriots, 35 Americans and 2 felons were chained together, put in irons and taken to the foot of Church Street. Here they were boarded on a steamer for the voyage to Kingston. Somewhat ironically this vessel was the Sir Robert Peel! (see TIL of April, 2013) According to John Stewart’s remembrances, on arrival in Kingston on a Sunday afternoon, the prisoners were compelled to walk from the harbour to the fort in irons, and at the same time carry their boxes on their shoulders. On arrival at Fort Henry, 15 rebel prisoners were put in one room next to the Officers’ Mess Kitchen. Here they were guarded by a gaoler and relays of soldiers.

Initially there was some hope for clemency. However these thoughts quickly changed and a plan for escape was hatched when the prisoners found a trap door leading to an underground passage. John Stewart recounted this discovery: “Although the walls were insurmountable, we had hopes of escape, judging that there was some underground passage if it only could be found. We used to pick up scraps of iron for use if necessary. The room next to ours was used by the 66th Regiment as a mess room before leaving for the West Indies. The door to this room was left open one day, and Leonard Watson going into the room, noticed a trap door and discovered to our great joy a subterranean passage.”

Lord Durham was expected to pass through Kingston on his way to Toronto on May 28. It was decided to delay any escape attempt until the rebels learned what the official response was to their petition for clemency. On his return to Toronto, Durham sent his aide-de-camp back to Kingston to tell the prisoners that he would lay the petition before Queen Victoria. Knowing that time was of the essence, it was decided that any further attempts using diplomacy would be abandoned. John Stewart concluded; “This was on a Thursday, and we determined then and there to help ourselves.”

John Montgomery echoed Stewart’s recollections and sentiments: “We had been but a small time in the fort, when through information given by persons kindly affected toward me, we learned that there was a possibility of our being enabled to effect our escape. This information we did not at first pay much attention to; but after Lord Durham had, on his arrival from Quebec, twice visited the fort, each time refusing our prayer for an interview, and when we had been told that any complaint should be in the form of a petition, we sent one down to Quebec and received for an answer a simple acknowledgement of its receipt, by Lord Durham, accompanied with an assurance that it would be forwarded to Sir George Arthur, in whom Lord Durham had the greatest confidence. We felt that it would be useless to look for mercy. And that we might at least make a venture. Accordingly, we organized a committee to investigate into the correctness of the information received and, hearing the former account substantiated, we began to make our arrangements.”

These details were corroborated by others who were involved. In one of the earliest published accounts of the escape, Stephen Brophy wrote about his experience in a letter to the editor in the August 8 edition of the Watertown [New York] North American. He added; “From all the subsequent observation and inquiry that lay in our power to make, an escape by mining a passage through this doorway appeared feasible; yet it was not till an answer was received from Montreal to an address presented to Lord Durham by a majority of the prisoners in the garrison, on his return from Toronto, stating that he (Lord Durham) had referred the address in question to Sir George Arthur, that a determination was agreed upon to place more reliance upon this passage and our own exertions, than in the Lieutenant-Governor or Lord Durham, in whose hands we lay.” In his remembrances, Thomas Shepard concluded: “A few days before the 29th of July he (Lord Durham) walked through our cell and told us that he had forwarded our petition. That didn’t satisfy us much, and when we heard that we were going to be shipped to Van Dieman’s (sic) Land pretty soon we thought we were not likely to get much good out of his Lordship’s forwarding our petition. We met that Sunday morning and decided to bolt.”

Work began in earnest to facilitate a mass escape. Thomas Shepard recorded that; “We were not long in prison before we commenced to think about getting out.” John Stewart’s memoirs detail the preparation and escape by 15 rebel prisoners: “The fort was so arranged that doors led from one room to the other. One side of the space for the door was built with stone. The thickness of the wall was six feet. We numbered the stones, and with the iron spike we picked out the mortar. The mortar we hid in the stove and the stones in our beds. Everything was carried on in the night time, so that on Saturday night the aperture through which we were to escape was completed. When all was quiet on Saturday night, having made a dark lantern of an old hat, we sent three of our men to examine the passage. When Parker came back he said it would be a miracle if any of us could get out. Next day was Sunday, and we were determined to try our luck at night.” Thomas Shepard added that; “Some of us worked all day trying to make the hole in the wall bigger. I was in that crowd, and the others tore her Majesty’s bedding into strips for rope ladders. At midnight we were all ready.” John Montgomery noted that; “We commenced on Tuesday and it was Sunday ere we had made a hole sufficiently large to enable us to get through.”

John Stewart continues with his recollections: “When all was ready, at midnight, we passed into the adjoining room, and getting into the subterraneous passage, we soon came to the gun room. The most perilous part of the work was yet to come, we had to descend from the gun room to the huge ditch below.....At last the signal was given, and we began to descend to the ditch according to pre-arranged numbers, each helping the other up. We were not to move until a signal was given by those who went to place the planks (the ladder) against the wall. The moon up to this time was shining brilliantly, but all at once a terrific storm of wind and rain broke out, as if to hide us from the soldiers close at hand. In going to the ladder, we were ordered to keep close to the inside wall, but Montgomery, instead of keeping up with the rest, strayed to the outer wall and fell into a ditch. He injured his knee so seriously that he had to be almost carried by us from that time.”

John Anderson, Stephen Brophy, Walter Chase, Edward Kennedy, John Mass, John Montgomery, Gilbert Morden, John G. Parker, Wilson Read, Michel Shepard, Thomas Shepard, John Stewart, William Stockdale, Thomas Tracy and Leonard Watson had successfully made their escape from the confines of Fort Henry. They made their way about 100 rods north of the Garrison and mustered, only to find out that John Parker was missing. Morden and Brophy did a quick search for him but soon returned and the group moved towards the river road to Gananoque. John Stewart was unequivocal about his feelings for Parker’s desertion: “He betrayed his comrades at the most critical time of our escape.” Parker was the only rebel who had lived in Kingston, and the only fleeing prisoner familiar with the area. He was to have taken the lead in reaching safety in United States. Brophy described the result: “Owing to the loss of Mr. Parker, our plan of arrangements for crossing the river was disorganized; and seeing Mr. Montgomery quite helpless and dispirited, myself and two others of our party volunteered to remain with him, and bring him away, or share his fate. The remaining ten divided themselves into two parties, and left for some favourable point down river.”

Official reaction to the escape was immediate. In a confidential report written by Major Richard W. Bonnycastle to his superior officer Colonel John Ross Wright on July 30, Bonnycastle provided detailed information about the escape. He identified John G. Parker as the ringleader, and suggested that the rebels “were aided by some person well acquainted with the passages to the reverse fires on that side of the Fort.” This allegation was corroborated by Leonard Watson who had been recaptured near Gananoque. The Cobou

rg Star in its August 15 edition reported that; “He (Watson) has made some statements by which it appears that one or two workers employed in the Engineering department had furnished the prisoners with their means of escape.” Bonnycastle implicated the fort’s master mason John Organ and casual labourer Richard Davis of assisting the prisoners in their flight. With the escape discovered, Fort Henry Commandant Colonel Sir Henry Dundas had gaoler John Ashley arrested. Subsequently John A. Macdonald assisted in defending Ashley. A judgement was made in his favour and damages of 200 pounds were awarded against Dundas for excessive detention without a warrant.


Mackenzie’s Gazette was one of the first newspapers to make mention of the escape. In the August 4 edition, it was reported that 15 rebels had escaped Fort Henry “by undermining the walls.” The following week private correspondence from Watertown, New York recorded that the majority of the escapees had arrived there. The article noted that Parker and Watson had been retaken and were again in confinement. Thomas and Michael Shepard and Wilson Read were soon expected in Watertown. The author concluded; “I cannot describe the delight they evince at being out of the fangs of Durham and Arthur.”

In an excerpt from the Upper Canada Herald printed in the August 18 Mackenzie’s Gazette, Toronto response to the escape was revealed: “Yesterday, Monday morning, our townsmen were astounded with the news that fifteen state prisoners had escaped during the previous night, which had been very stormy. They had been furnished with a plan of the fort, which, it is believed, has been drawn by someone who had access to the plans in the Engineer department. They had also obtained a mason’s setting bar, which had been recently pointed with steel by a blacksmith in the works. Thus furnished, they broke through the partition wall between their cell and the adjoining one. This wall was four feet thick, and had a door connecting the two cells, which door way had been walled up, and through this they broke. This other cell had a trap door leading to the covered way which goes into the ditch of the fort. They then made their bed-boards into ladders by tying them together with sheets, and mounted the wall of the ditch and escaped.” In the same edition of Mackenzie’s Gazette, it was reported that the majority of escaping prisoners had reached New York State and were residing in Oswego and Watertown. The [Sandwich] Western Herald reprinted Brophy’s first-hand account in its September 11 edition. Editor Henry Grant added caustic remarks about what he labelled as Brophy’s “bombastic production.” He proceeded to illustrate that Brophy was “thoroughly versed in the art of lying” in much of what he had to say about the escape.


Brophy wrote to William Lyon Mackenzie from Monroe, Michigan on August 4, 1839. This letter was reproduced in the August 17, 1839 issue of Mackenzie’s Gazette. In concluding his remarks, Brophy made the following observations: “I can hardly close this letter without an illusion to ‘the impregnable Fort Henry.’ On this morning 12 months ago, the strong walls of that celebrated fortress was discovered to be perforated and crumbled into dust, by a few emaciated and apparently exhausted men inside, who had flown-and while I deeply commiserate your condition, knowing well what feelings are awakened in us, on being deprived of the free air of heaven-in observing the anniversary of my freedom, the recollection of every incident connected with it is yet vivid on my mind, and perhaps nothing more so the undying hatred to men of misrule, with which some of us left the province. At present, I am one of the very many in this country who as the law now stands, should reside on the disputed boundary-being claimed by both sides. I wish most heartily that Mr. Van Buren and the Queen would fight it out, as I hope to be a looker on till the point is settled, and I should recommend all who are called upon by this double allegiance to do the same.”

The solution to Brophy’s quandary and that of his fellow Fort Henry escapees, came not by violence but through a decision made early in 1843. Sir Charles Metcalfe, the Governor General of Upper Canada, issued a general amnesty for all charged with their involvement in the 1838 rebellion. Some of the exiled rebels chose to stay in United States, while others returned to Upper Canada to resume their lives as free men. For the 12 men who had successfully escaped from Fort Henry, their long and eventful story had finally come to a close. Yet another chapter in the Patriot Chronicles!

By Dr. John C. Carter,

Dr. John C. Carter is an Ontario historian, museologist  and a Research Associate at the History and Classics Programme, School of Humanities, University of Tasmania. This is his sixth article written for TI Life (Click here view his other articles).   In particular his February 2013 Patriot Chronicles: The Hickory Island Incursion and April 2013 The Burning of the “Sir Robert Peel”…

In addition Dr. Carter has provided a bibliography to study this important era of  Thousand Islands history which can be found in THE PLACE, History page.

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Peter Starr
Comment by: Peter Starr ( )
Left at: 2:13 PM Monday, July 15, 2013
Excellent article !
Shaun McLaughlin
Comment by: Shaun McLaughlin ( )
Left at: 9:21 AM Tuesday, July 16, 2013
Excellent detail and great to read so many first-hand accounts.
Comment by: J.MacKinnon ( )
Left at: 8:20 PM Thursday, July 18, 2013
Great article , John. Such brave men and to
think John Stewart eventually ended up in the
small village of Paisley, Ontario co-owning a