John Montgomery (1788–1879) was born in Gagetown, New Brunswick, the son of Alexander Montgomery. Alexander immigrated to New Brunswick after the American Revolutionary War. In 1798, the Montgomery family moved to York, Upper Canada, where over time, Alexander and John operated several taverns.
Montgomery’s Tavern was opened in about 1830 on Yonge Street, in the area of Eglinton. Sometimes known as the Sickle And The Sheath, it was described as “a large wayside inn, with a broad platform in front, and a lamp suspended over the central doorway.”
Montgomery supported the Reform movement, which opposed the cronyism and patronage prevalent in the politics of Upper Canada. He helped finance William Lyon Mackenzie's travels to England to present petitions for change to the Colonial Office. Montgomery also participated in the founding of the Bank of the People. He also signed a declaration of Toronto Reformers and was a member of a vigilante committee tasked with carrying out its resolutions.
By the spring of 1837, it appeared to Reformers that all constitutional avenues for political change were blocked and a more active resistance was required. Reformers became victims of attacks from gangs affiliated with the Orange Order. At the same time, Mackenzie was attracting large crowds for political meetings and for shooting practice. He concluded that the most logical course of action was to lead the crowds into Toronto to occupy the government assembly and detain the Lieutenant-Governor, Sir Francis Bond Head.
Mackenzie set Thursday, 7 December for the uprising, and selected Montgomery’s Tavern as the rendezvous point. As early as Monday, protesters began collecting at the tavern.
Montgomery was asked to provide the gathering force with food and other supplies, a task that he refused. Montgomery was surprised by the request, as by that time he had leased the tavern out to John Linfoot. Although Linfoot had not yet legally taken possession of the tavern, he had already moved in. However, Montgomery still occupied one of the rooms of the tavern. Montgomery’s reaction should not have been unexpected. He'd had a falling out with Mackenzie, had not taken part in many recent meetings, and was ill-informed about the rebellion's plans.
Mackenzie organized three lines of rebel pickets to the north, south and directly across from the tavern, to prevent loyalists travelling south from carrying information into Toronto. Prisoners detained by these pickets were held in the tavern.
By Monday night, approximately 90 protesters had arrived at the tavern, only to find they had no food. Linfoot, the new proprietor of the inn, was a Tory — sympathetic to the government — and thus would not provide provisions without prepayment. This forced Mackenzie to delve into a meager fund previously raised in order to provide a light supper. The next day, Tuesday, 5 December, under coercion, Montgomery agreed to supply the insurgents with food.
Battle of Montgomery’s Tavern
Later on Tuesday, Mackenzie marched 800 untrained rebels south on Yonge Street to the city, only to be repulsed by a picket led by Sheriff William Jarvis at what is now the intersection of Yonge and Maitland streets, near present-day College Street. This caused a defection of protesters over the next two days, who were not expecting an armed uprising.
The number of new arrivals at the tavern could not match those departing, and so by 7 December, the insurgents amounted to only 500 men. They were ill-equipped to meet 1,000 militia and volunteers ordered north under Colonel James FitzGibbon to put down the rebellion. About 150 rebels, armed with pikes and rifles, were posted to the woods west of the inn; another 60 were posted in fields to the east. The remainder — unarmed and of little strategic use — mulled about outside the tavern or took shelter inside.
When FitzGibbon's force arrived at the tavern, the skirmish lasted for 15 minutes. FitzGibbon had two cannons which quickly dispersed the insurgents. Two cannonballs passed through the tavern. Before the building was taken, loyalist prisoners held since Monday were led out the back by the insurgents and freed.
Lieutenant-Governor Bond Head, while pardoning many of the rebels immediately after the battle, ordered the tavern to be burned to the ground. Only one rebel, Ludwig Wideman, died at the tavern during the battle, while a number of other insurgents and a few loyalists were wounded.
After the fighting, Montgomery was arrested and charged with high treason. Found guilty, and sentenced to be executed, his sentence was commuted. En route to Fort Henry, he escaped and fled to Rochester, New York, where he once again encountered Mackenzie. He was pardoned in 1843.
On his return to Toronto, Montgomery began submitting petitions for compensation for the loss of his tavern, but was not successful until 1873. At that time, a committee of the Legislative Assembly under Oliver Mowat determined that Montgomery’s loss exceeded $15,000. His compensation was $3,000.
In the decades after the rebellion, the Montgomery's Tavern site was the location of several hotels, before the land was acquired by Canada Post. Postal Station K occupied the location, until the post office property was sold in 2012. On 15 May 1925, a historic plaque was placed at the site — a plaque now maintained by the Historic Sites and Monuments Board of Canada.
There are no known remnants of the pre-1837 tavern. Even its exact location and footprint have been lost.
(Note: Montgomery’s Tavern should not be confused with Montgomery's Inn in Etobicoke, which operated in the same historical period and was owned by Thomas Montgomery — no relation of John Montgomery.)