The Battle of the Windmill

When we last left off, the refugee rebel mayor of Toronto, William Lyon Mackenzie, had just been driven from his declared Republic of Canada on Navy Island, which helped rally Americans to his side and started a year-long series of battles and invasions known as the Patriot War.

Violence begets violence, often in ways that are hard to predict in the moment. As Upper and Lower Canadians rebelled, Americans were watching. And what they saw were oppressed Canadians, fighting for their freedom from British tyranny. The rebellions looked to many Americans like a northern version of their own Revolutionary War. Defeated Canadian rebels fled to the United States, exploiting a legal loophole known as “this border isn’t tightly controlled yet,” and their stories inspired would-be American liberators to rally to their side.

The Upper Canada Rebellion took place at the end of 1837 in December, and the Republic of Canada occupation of Navy Island ended in January 1838. In May, a secret group called the Hunters Lodge, comprising both Canadian rebels and sympathetic Americans, formed to build up an army and plan an invasion of Canada. In September they “held a convention in Cleveland, Ohio, to pick new leaders for pending invasions of Canada that fall,” writes Shaun J. McLaughlin in The Patriot War Along the New York-Canada Boarder (from which this post draws heavily).

Formed in the style of masonic secret societies, members in the Hunters Lodge held one of four levels of membership: “snowshoe, beaver, master hunter and patriot hunter.” The Hunters had at least $150,000 and “large stores of arms.” They “bragged that they had twenty-five thousand armed men ready to fight,” but that would prove overly-confident.

The Patriot War included many small plots, invasions, and skirmishes, but the Hunters’ decision in the fall of 1838 to invade Prescott, Ontario was “one of the worst decisions” of the war, writes McLaughlin, and led to its bloodiest battle.

Thanks to a spy, the Upper Canadians were expecting an attack in Prescott, which is on a narrow stretch of the Saint Lawrence River near Kingston, where the Canadian and US sides are easily in view of one another. The Hunters didn’t know about the spy, but their leaders did know that not nearly enough men had shown up for the invasion. Despite suspecting “our scheme will fail,” the leaders conversed and agreed to press on. “I’d prefer to be shot” than back down, said one. “I would rather die than be branded a coward,” agreed the other.

The Hunters had managed to assemble 400 men split over three boats, which were lashed together and steaming towards Prescott from the American side. But when the moment of truth arrived, and the men were ordered to all consolidate onto the two smaller boats that would land on the north side of the river, only half of them agreed.

Under the cover of darkness, the first attempted landing went hilariously wrong. Both schooners approached the Canadian shore, lashed together. “As they came upon the wharf,” one man jumped out, tied a rope, and then jumped back in “just as the rope broke.” As the sun rose the next morning, people on both sides of the border “witnessed the embarrassing result of the Hunters’ aborted raid:” the schooners were both beached near the shore on the American side.

The next morning the invading force did successfully land on the Canadian side with men and artillery, on “a point one mile downstream from Prescott” near the battle’s eponymous windmill. “They immediately took possession” of the windmill and raised a flag that boasted Canada had been “liberated” by the Hunters.

They really believed “that Canadians would flock to the Hunters as liberators.” Reader, the Canadians did not. Upper Canada, and especially Prescott, was full of British loyalists, because of the thing where the Americans had fought a whole war against the British, strongly incentivizing any loyalists in The Thirteen Colonies to head north.

In addition to the windmill, the Hunters soon held “the barn and all unoccupied buildings” as “most residents fled.” Meanwhile, a small naval battle flared-up on the Saint Lawrence, as two ships played cat-and-mouse back and forth across the boarder. The British ship was called the Experiment, and the ship that had been captured for use by the Hunters was called the United States.

Ultimately the two ships charged each other, seemingly playing chicken. The Experiment swerved at the last second and “fired at close range… removing half of [the United States‘s captain’s] head.”

At this point, the Hunters had picked fights with loyal Upper Canadians, the British military, and the U.S. military, because they were in violation of the U.S. Neutrality Act, which made it illegal for any American to go to war against a power that was at peace with the U.S., which Britain was. Soon U.S. troops had arrived on the U.S. side, and “an American steamer… patrolled in mid-river to prevent any further crossings.”

With that, “the trapdoor” closed. Throughout the night rowboats went back and forth “carrying men in both directions” as some people deserted and others joined the fight, but by the morning the 182 Hunters who occupied stone buildings on the Canadian side of the river were stuck, without hope of reinforcement, and with both the British military and Canadian militia closing in.

Find out what happens next in the third and final post in this series, The Hunters become the hunted.