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 .