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Charlotte de Grassi's father, Phillipe de Grassi
Charlotte de Grassi's father, Phillipe de Grassi

Cornelia de Grassi and the Upper Canada Rebellion: A Tale of Old North York

A thirteen-year-old girl, in acts of derring-do, helped the government side win in the 1837 Upper Canada Rebellion.

Cornelia de Grassi was the daughter of Phillipe de Grassi (shown in picture), descendant of a noble Italian family, who settled in what is now the Don Mills-Lawrence Avenue East area, on a 200-acre grant in 1831. He was a supporter of the government side in Upper Canada and wrote in his diary, “After a fire (in 1833), I managed amidst great trials and difficulties to struggle on until that unfortunate rebellion broke out in 1837 when Mr. W. L. Mackenzie thought to take upon himself more regal functions and declared that my property with that of many other loyal men should be parceled out among his followers.”

On the evening of December 4, 1837, when the rebellion broke out, de Grassi went to Toronto with his daughters, Charlotte, age 15, and Cornelia, age 13, to offer his services to the government and governor, Sir Francis Bond Head. He volunteered to discover the strength of the rebel party. Head accepted the offer and de Grassi, instead of doing the spying himself, asked Cornelia to do it, perhaps figuring that the rebels would not be suspicious of a child.

De Grassi wrote about her daring expedition in his diary, “Cornelia, a capital rider, rode out under the pretense of wishing to know the price of a sleigh, went to the wheelwright’s shop close to Montgomery’s tavern, and being suspected was taken prisoner by some of the rebels who ordered her to dismount.”

Despite the danger, Cornelia was unflustered. Luckily for her the rebels’ attention was soon distracted when Mackenzie announced that the western mail had been captured by the rebels. In the confusion and rejoicing, Cornelia had the presence of mind to gallop away as several muskets were fired at her. She barely escaped alive. One musket ball went through her saddle and another grazed her clothing.

Arriving back in Toronto, she passed on crucial information as to the number and condition of the rebels. She reported that the number of rebels had been greatly exaggerated. This information was invaluable for the government forces in dealing with Mackenzie and his supporters. “Thus the Loyalists were encouraged, measures were taken to meet Mackenzie’s attack and so my poor child was the means of saving Toronto where he had many partisans,” her father wrote in his diary. Based on her information about the relatively small number of rebels, Sir Francis Bond Head, who had previously been so sure of defeat that he had put his family on board an England-bound steamer, revised his thinking and decided to hold out.

The heroic Cornelia’s adventures did not stop here. After following the government “loyal” troops up Yonge Street, she was on her way home when she discovered rebel Peter Matthews setting fire to the Don Bridge. Again she returned to the city and gave the alarm.

He was captured soon afterwards and was later hanged for treason.

Charlotte de Grassi had her share of excitement, too. Returning from Toronto, she was fired upon and wounded by a large party of rebels.

NOTE: De Grassi Street, off Queen Street East, near Broadview Avenue, and the popular TV series, are both named after this family.

By Susan Goldenberg, Director, North York Historical Society

Originally published in the August-September 2013 North York Historical Society Newsletter