Battle of Montgomery's Tavern

The Battle of Montgomery's Tavern was an incident in the Upper Canada Rebellion. The abortive revolutionary insurrection inspired by William Lyon Mackenzie was crushed by British authorities and Canadian volunteer units near a tavern on Yonge Street, Toronto.

The site of Montgomery's Tavern was designated a National Historic Site in 1925.

Prelude
When the Lower Canada Rebellion broke out in the Fall of 1837, Sir Francis Bond Head sent the British troops stationed in Toronto (formerly York) 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 Yonge St just north of Eglinton Avenue – the present-day site of Postal Station K) on December 4, 1837.

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. They were met by a truce party, to whom Mackenzie explained the rebels' demands.

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 loyalist men fired a volley then dropped to reload their guns. Mackenzie's men ran towards them, believing they had killed the loyalists. They met the loyalist fire unprepared. The rebels dispersed, losing hundreds of deserters. That night, reinforcements for the loyalists arrived from Hamilton. By the next day, these forces were 1,500 strong.

Montgomery's Tavern
The rebels, under the command of 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 (1832–?), 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, the vacant land was sold to proprietor (and later as hotelier) John Oulcott of Toronto, who rebuilt a three storey Oulcott's Hotel (Eglinton House) 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 cypher EviiiR, for Edward VIII, King of Canada for eleven months in 1936; it is one of a few buildings to bear this mark in Toronto.