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War of 1812: The story of Joseph Shepard, who risked his life in Battle of York

Captain Neal McNeale falls at the head of a small band of men from his grenadier company, of the 8th King's Regiment of Foot, while attempting to delay the much larger American force as they storm ashore.



“Their faces were completely black . . . their hair frizzled . . . and their clothes scorched and emitting an effluvia so strong as to be perceived long before they reached one.”

Patrick Finan Jr.

describing the soldiers wounded in the explosion of a portable magazine

On the morning of April 27, 1813, Joseph Shepard would have awakened in a two-storey, military blockhouse near what’s now the intersection of Parliament and Front Streets.

All around him were fellow members of the 3rd Regiment, York Militia, but few could boast the battlefield resumé that Shepard had already built, having borne witness to some of the most pivotal events in the opening stages of the War of 1812.

As part of the rifle company of the 1st York, he’d almost certainly taken part in the capture of both Mackinac and Detroit, and he was with the flank company of the 3rd York in repelling the American invaders at Queenston Heights.

Now, on a cool spring day 200 years ago, he was about to risk his life again, and this time he would very nearly lose it.

His story, like that of so many ordinary combatants on either side, emerges today from a jumble of knowns and unknowns, the mixing of fragmentary documentation and conjecture.

But it illuminates how a typical farmer and soon-to-be-wealthy mill owner could get caught up in a bitter war that, while tiny compared with the Napoleonic struggle in Europe, nevertheless shaped a continent — pitting brother versus brother, cousin against cousin.

Had he died, his passing would not have altered the outcome of the Battle of York that day, when American invaders ransacked what’s now Toronto.

But his early death would still have had historical repercussions, since in later life he became a leading member of the reform movement that culminated with the 1837 Upper Canada Rebellion, the Durham Report and responsible government, this country’s constitutional gift to the British Empire.

The other repercussion, had Shepard died in battle, is that he wouldn’t have been around to provide for a family that by then numbered six young children, one of them in a line that descends to yours truly.

Joseph Shepard was my great-great-great-great grandfather.

Perhaps fittingly, it was another military struggle that had brought Shepard to Canada in the first place.

Born in New Hampshire in 1767, he’d come as a youngster to what are now Quebec’s Eastern Townships with his Loyalist family in the wake of the American War of Independence.

He could have joined the family milling business, but he seems to have had an early taste for adventure.

After first removing himself to the Loyalist heartland of Prince Edward County, Shepard appears to have set out as a fur trader sometime in the 1780s.

The newspaper obituary for one of his sons, Joseph Jr., claims that as early as 1785 Shepard Sr. had set himself up near the Toronto Carrying Place, the fur-trading trail that ran from Humber Bay on Lake Ontario to Lake Simcoe.

No contemporary portraits of Shepard appear to survive, but he seems to have been an imposing figure.

In a front-page obituary in The Constitution newspaper in 1837, William Lyon Mackenzie wrote:

“Mr. Shepard’s countenance was open and manly — he was remarkably good natured — his stature was six feet, and he was stout built in proportion.”

By 1796, he was applying to the Crown for a land grant in what’s now North York. He’d soon be buying many more farms in the area, and setting up lumber and grist mills on the Don River.

As the War of 1812 approached, Shepard ran for a seat in the legislative assembly, campaigning against Maj.-Gen. Isaac Brock’s plan to suspend habeas corpus for the duration of hostilities.

It foreshadowed the democratic reformer he’d later become. Shepard simply believed that habeas corpus — the legal right of any accused to be brought before a judge — was too fundamental to be withheld, even in a time of war.

He lost, and soundly, to the government candidate, Thomas Ridout, and was soon enough joining the rifle company of the 1st York Militia.

At the time, British regulars and Canadian militia mostly fired muskets, which are impossible to aim with any kind of precision. But they are quicker to load — a top British regular could fire three times a minute — and they produced the intimidating wall of lead upon which the British relied.

Rifle companies, by contrast, were made up of marksmen, and Shepard’s time as a fur trader would undoubtedly have made him a very, very good shot.

He enlisted as a private and was never an officer, which at first blush seems odd, since in so many respects he fits the officer bill. Loyalist, Anglican and increasingly wealthy, his grist mill was by then probably provisioning the British garrison.

It could be that he was illiterate, since officers had to read massive manuals on drilling and battlefield deployment. But given his political and church activities, it’s far more probable that he could, in fact, read and write.

A better explanation is that the officer corps was already well stocked by the time Shepard arrived. And even if a spot had opened, Shepard might not have been a natural choice, given his staunch opposition to Brock’s plans for habeas corpus.

In one of those ironic twists of history, Shepard would eventually wind up with Capt. Samuel Ridout’s company, 3rd York — Samuel being the son of Thomas, Shepard’s electoral adversary.

It’s with Ridout’s company that Shepard awoke in the town blockhouse on April 27, a day of destiny for both him and the capital of Upper Canada.

The American invading force set sail from Sackets Harbor, N.Y., on April 25 and they appeared at daybreak two days later off the peninsula that would eventually become Toronto Island.

On board those 14 ships were roughly 3,000 soldiers and sailors, a number that dwarfed the 500 or 600 British regulars, Canadian militia and Indians that Maj.-Gen. Roger Hale Sheaffe had at his disposal.

Sheaffe expected the Americans to land both east and west of town, which explains why his forces were scattered in both directions.

Instead, the American flotilla appeared en masse to the west of York, near today’s Toronto Island airport. But a strong easterly wind soon blew them much further west, out toward the Humber River, before they could start sending troops ashore.

The British 8th Regiment had already gone off to challenge the American landing when Shepard’s group was ordered to hurry westward.

En route they encountered what Isaac Wilson, a private in the 3rd York, later described as “the wounded men, some (going) one way and some another, and such a bloody sight made me wish for the first time that I was safe at ‘Birkbank’ again.”

This is where the exact shape of any militiaman’s day, including Shepard’s, starts to get fuzzy.

“We don’t know what’s going on at a level of detail that’s going to tell the story accurately,” says Richard Gerrard, historian with the City of Toronto’s museum services.

Militia members ended up “all over the map” amid much confusion, and there were never any complete lists of all the men engaged in battle that day or precise accounts of their movements.

The main clue about how Shepard’s day unfolded is a medical report, dated Feb. 19, 1816:

“I do hereby Certify that the Bearer Joseph Shepard was dreadfully wounded on the 27th April, 1813, at York, by the Explosion of the Magazine: his left thigh was much mangled: the wound is not yet healed up — and he had three of his Ribs broken on the left side.”

The note is signed by Robert Hertz, Surgeon, Indian Department.

To Gerrard, this raises some interesting possibilities. Did Shepard have some sort of role with the Indian Department, which was instrumental in securing Indian support for the British?

From his days as a fur trader, Shepard would certainly have been a known figure to local Indians, but it’s unclear why someone from the Indian Department would be examining him.

The surgeon’s note is also silent about where in the field of battle Shepard sustained his injuries, nor does it clearly specify which of two magazine explosions did the damage.

This is where the conjecture comes in.

Richard Feltoe, avid War of 1812 re-enactor and author of such books as Redcoated Ploughboys, is standing in the parking lot of the Argonaut Rowing Club on Lake Shore Blvd. W.

From here, it’s easy to survey the shore of Lake Ontario to the west, towards the Humber River, where American troops began coming ashore, 300 at a time, around 7 a.m.

The British regulars who had gone out to contest the landing, supported by Indians in the woods to the north, were soon vastly outnumbered.

So they began a fighting retreat to the ruins of Fort Rouillé, built by the French in 1750, just east of where a giant wind turbine now stands on the grounds of the CNE.

On the mostly open plain surrounding the fort, the regulars and militia would make their next stand, the retreating 8th joined there by the Royal Newfoundland Regiment and sundry militia.

For at least an hour, the two sides traded close-range volleys along a line that ran from the lake to what is today the Queen Elizabeth Building.

It was a scene of carnage, the butcher’s bill steep. By the end of the day, the 8th Regiment alone had suffered casualties at the astonishing rate of 65 per cent.

Shepard could have been there alongside the 8th, arriving either directly or with the militia units that had originally gone with the Glengarry Light Infantry to guard a second, inland path from the Humber to York along what was then an extension of Lot St., now Queen St. W.

But Feltoe thinks this unlikely, and even if Shepard had been at the Fort Rouillé fight, it’s not where he sustained his wounds.

The British and Canadians then began a further, fighting retreat towards the western gun battery, about where the Princes’ Gates now stand.

By then, the American ships had moved eastward and begun shelling the defenders in earnest. Yet the most lethal damage was self-inflicted, when a portable magazine at the western battery accidentally blew up.

More than 30 men were instantly killed or wounded.

Patrick Finan Jr., a 12-year-old at the time, had sneaked out of his family’s house to catch a glimpse of the battle, and soon came upon those wounded in the explosion as they staggered back toward Fort York, which was then on the east side of today’s Bathurst St. rather than its post-1813 location to the west.

As Finan wrote in Recollections of Canada, published 16 years later:

“Their faces were completely black, resembling those of the blackest Africans, their hair frizzled like theirs, and their clothes scorched and emitting an effluvia so strong as to be perceived long before they reached one.”

Shepard could have been among them, and Feltoe thinks the nature of his wounds suggests fairly close proximity to an explosion.

But there are still other possibilities, since most of those killed by this explosion were British grenadiers.

With the loss of the western battery, Sheaffe now realized his only option was a full retreat, eventually to Kingston, lest his British regulars be lost to the enemy.

The militia, meanwhile, returned to their appointed assembly area in the ravine behind Government House, roughly the rail corridor just north of present-day Fort York.

But the gathered militia had no idea what was coming next.

To the south of Government House, near the then-shore of Lake Ontario, sat a magazine stocked with more than 30,000 pounds of powder.

The Americans were by then readying to march into town, so Sheaffe ordered the magazine detonated — a noon-hour blast that spread more than 450 metres and even damaged some American ships.

In a letter penned soon after the battle, Abraham Eustis, a major with the U.S. army, described the scene as “horrible, more awful, and, at the same time, more sublime, than my pen can portray.

“At first the air was darkened with stones, rafters, and clay. In about half a minute the infernal shower descended and dealt destruction to our column. Hardly a man escaped without a bruise; 250 were either killed, or seriously wounded.”

Among the American dead: Brig.-Gen. Zebulon Pike.

Although the main body of militia in the ravine would have been shielded from the initial blast, lots of debris would have rained down on them.

So it’s possible that, having heard the initial blast, Shepard hit the ground and was then struck by the fallout.

Most contemporary accounts mention a lot of falling stone, giving rise to the belief that the magazine was a massive stone structure, which is how it gets depicted in drawings made much later.

There’s just one problem. In all the excavations done at the site, archeologists have found scarcely any large stones.

Instead, they’ve encountered copper nails, the metal hoops that would have held together wooden barrels of powder, and broken bricks, not to mention the grapeshot the Americans had fired from their ships.

Gerrard thinks all that points instead to a temporary rather than stone magazine, a description Brock himself had earlier used.

A temporary British magazine of that era was typically built with heavy timbers and copper nails and a flat roof covered in bricks. Earthworks would then have been heaped on top.

Which brings Gerrard to an alternative theory: Shepard was likely among the militia stationed at another gun battery just east of the magazine, closer to today’s Bathurst St.

The initial blast of debris would have hit him directly.

Shepard was soon a wounded prisoner of war, though he’d be paroled — essentially let go on condition that he take no further part in the war.

The medical treatment he received would have been anything but quick and sophisticated, the tools of a surgeon’s trade then resembling those of a carpenter.

As William Beaumont, a surgeon with the U.S. army, recorded in his diary on April 27, 1813:

“The surgeons wading in blood, cutting off arms, legs, trepanning heads to rescue their fellow creatures from untimely deaths.”

The scene, he wrote, would have “shocked the insensibility of the most hardened assassin and the crudest savage.”

With Sheaffe departed, local command fell to Lt.-Col. William Chewitt and Maj. William Allan of the 3rd York Militia, who had the task of negotiating the terms of capitulation.

Ostensibly, those terms called for private property to be respected, but in reality American troops wandered through town, going into homes and hauling away whatever loot they fancied.

To York’s Anglican rector (and later bishop), John Strachan, it all amounted to “indiscriminate pillage & conflagration.”

The parliament buildings of Upper Canada’s capital were burned to the ground. The professed reason: a couple of U.S. sailors became incensed when they saw a human scalp draped over the parliamentary mace.

This seems hard to credit. But that doesn’t mean there wasn’t a scalp in the building.

Robert Gourlay, in an 1822 book, wrote how a scalp had been sent along with a letter to the clerk of the assembly by one of the clerk’s military friends, thinking it a curiosity.

“Upon opening the letter, he and two or three others who happened to be present were disgusted at the sight, and he threw the letter into an under drawer of his table.”

The Americans duly left York several days later, and Shepard would have eventually returned to his home near what’s now Yonge St. and Sheppard Ave.

As was the custom, the Crown granted Shepard still more land in return for his military service, but his earlier opposition to any suspension of habeas corpus may be what cost him another honour.

In the wake of the war, a Loyal and Patriotic Society was created through private subscription to provide pensions for veterans of the war.

Strachan, a great admirer of Brock and the soon-to-be Anglican bishop, effectively controlled the society and the distribution of any funds.

So perhaps it’s not completely surprising that one name is conspicuously absent from the list of pensioners: Joseph Shepard.

It may, however, be a measure of Shepard that the snub wasn’t about to stop him from donating the land for St. John’s Anglican Church, York Mills. Built initially of wood, the church’s ceremonial “cornerstone” was laid in 1816 by none other than John Strachan.

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