John Montgomery (probably February 29 1788 – October 31 1879) was a Canadian tavern‑keeper and local political figure in Upper Canada (later Ontario). He is most noted for his ownership of Montgomery’s Tavern on Yonge Street, which served as the rebel headquarters during the Upper Canada Rebellion of 1837 and was the site of the Battle of Montgomery’s Tavern.
Early life and military service
Born in Gagetown, New Brunswick, Montgomery was the son of Alexander Montgomery, a former resident of Stamford, Connecticut, who migrated to New Brunswick after the American Revolutionary War. In 1798 the family relocated to York (present‑day Toronto) in Upper Canada. During the War of 1812, Montgomery served on the Niagara frontier and participated in the Battle of Queenston Heights.
Business activities
Montgomery operated several taverns in the York area. In 1828 he ran “The Bird in the Hand” at Yonge Street and Finch Avenue. He leased this inn in 1830 and began construction of a new establishment, Montgomery’s Tavern, further south on Yonge Street. The tavern became a well‑known gathering place for reform‑oriented citizens.
Political involvement
Sympathetic to the Reform movement, Montgomery assisted William Lyon Mackenzie in traveling to England in 1832 to present petitions to the British Colonial Office. He was a founder of the Bank of the People (1836) and served as a road commissioner for York County and a director of the Mutual Insurance Company. Although he signed a declaration of Toronto Reformers and joined a vigilance committee in July 1837, he did not advocate open rebellion.
Upper Canada Rebellion
In December 1837, authorities designated Montgomery’s Tavern as the rebel base. Montgomery was appointed commissary for the rebels, though he was in the process of moving out of the premises. On December 7, 1837, under orders from Lieutenant‑Governor Francis Bond Head, the tavern was burned. Montgomery was arrested, charged with high treason, and initially sentenced to death; the sentence was later commuted to exile. He was sent to Fort Henry pending transportation to Tasmania, but escaped to Rochester, New York, where he led an association for Canadian refugees. After receiving a pardon, he returned to Toronto in 1843.
Later life
Upon his return, Montgomery rebuilt a new tavern on the original site and continued operating several taverns in Toronto, including a hotel at the northeast corner of Church Street and Colborne Street. In 1871 he moved to Headford in Markham Township, serving as postmaster until 1876. He later relocated to Barrie, where he died in 1879 and was buried in Union Cemetery.
Legacy
The site of Montgomery’s Tavern, now a post office location, was designated a National Historic Site of Canada in 1925. Montgomery’s role in the 1837 rebellion and his contributions to early Toronto commerce are recognized in Canadian historical scholarship.