When the Lower Canada Rebellion broke out in the fall of 1837, Sir Francis Bond Head sent the British troops stationed in Toronto to help suppress it. With the regular troops gone, William Lyon Mackenzie and his followers seized a Toronto armoury and organized an armed march down Yonge Street, beginning at Montgomery's Tavern on December 4, 1837. While marching down Yonge Street, Mackenzie and some fellow rebels encountered John Powell and Archibald McDonald while attempting to scout the city. Upon meeting them, Mackenzie took Powell prisoner and sent them to Montgomery's Tavern. Although there were concerns over whether Powell and McDonald possessed arms, Mackenzie accepted their denials and said, "well, gentlemen, as you are my townsmen, and men of honor, I would be ashamed to show that I question your words by ordering you to be searched." Despite such assurances, Powell had hidden a pistol and shot rebel Captain Anthony Anderson before escaping back to Toronto, thereby dealing a large blow to the rebel's military expertise. Colonel Robert Moodie attempted to lead a force of loyalists through the rebel roadblock to warn Governor Bond Head in Toronto. Moodie fired his pistol, apparently in an attempt to clear the way. A number of the rebels returned fire, killing him. On the same day, December 5, Mackenzie's approximately 500 rebels marched upon Toronto's city hall in an effort to seize the arms and ammunition that were stored there. As Mackenzie and his forces marched towards Toronto, Bond Head sent a flag of truce and asked for their demands, to which Mackenzie demanded "Independence and a convention to arrange details." By the time Mackenzie and his followers had reached College Street, Bond Head sent another party to tell Mackenzie that his demands had been rejected. Later that afternoon, Mackenzie led his troops farther down Yonge Street towards the city, where their advance was stopped by a party of 27 loyalist volunteers, led by William Botsford Jarvis. The two sides exchanged gunfire. Jarvis' loyalist troops fired a volley at Egmond's gang and dropped to reload. Thinking the loyalist soldiers had been killed, Van Egmond gave the order to charge and in the ensuing melee many of the rebel soldiers fled or deserted the group. That night, reinforcements for the loyalists arrived from Hamilton. By the next day, these forces were 1,500 strong. The last real engagement prior to the Battle of Montgomery's Tavern occurred on December 6 via a raid on a mail coach which was suspected to have government intelligence regarding future actions towards the rebels. It was from this raid that the rebels learned of government plans to soon attack Montgomery's Tavern.
Montgomery's Tavern
The rebels, now under the command of Napoleonic Wars veteran Anthony Van Egmond, had regrouped at Montgomery's Tavern. One hundred and fifty were posted in the woods behind the tavern and another 60 took up positions behind a line of rail fencing. The majority of Mackenzie's supporters, numbering about 300, were gathered around the tavern proper. These were largely unarmed and would offer little resistance when pressed. On December 7, Colonel James Fitzgibbon marched an estimated 1,000 regulars and militiamen up Yonge Street and attacked Mackenzie's force at Montgomery's Tavern, putting the building under artillery fire. When Fitzgibbon advanced his infantry, both parties of rebels abandoned their posts and retreated in disarray to the tavern, causing those assembled there to panic and flee. Within 20 minutes, the rebels were gone. Loyalist forces then looted the tavern and burned it to the ground, before marching back to York.
Post rebellion and site today
Following the rebellion, the site of the tavern was used to build a hotel, with the structure of the old Davisville Hotel. In 1858 it was sold to hotelier Charles McBride of Willowdale, who renamed the tavern Prospect House. The tavern would serve as Masonic Lodge and North Toronto township council office. McBride sold the hotel in 1873 to build another hotel, Bedford Park Hotel, on Yonge Street. Prospect House burned down in 1881, and the vacant land was sold to proprietor John Oulcott of Toronto, who rebuilt a three-storey Oulcott's Hotel in 1883. Oulcott sold out in 1912 and the hotel went to various owners. In 1913, the federal government purchased the hotel and remodelled the old hotel as a post office for the North Toronto postal district. It was finally torn down in the 1930s to be replaced by the current structure. The site of the tavern is now occupied by a two-storey Art Deco post office designed by Murray Brown and built in 1936. The building, Postal Station K, bears the cypherEviiiR, for Edward VIII, King of Canada for eleven months in 1936; it is one of a few buildings to bear this mark in Toronto. As of spring 2016, construction is underway to incorporate the post office into a new building which will include retail space and podium for the 27-storey Montgomery Square luxury rental apartment building.
