Isaac Dollery (1835-1924) was a notable North York eccentric.
There are lots of enjoyable stories about him, some perhaps exaggerated, in NYHS’ archives now at the North York History Room, 5th floor, North York Central Library.
According to one story, one day Dollery, a carpenter by trade, brought home a bear cub after killing its mother. He kept it as a pet, boxing with the animal and taking it for walks on a chain. Someone offered him $200 for the cub if its weight could be increased. That was a lot of money in those days and Dollery was determined to earn it. However, he fed the cub so much that it died before he could collect the money.
Dollery was reputed to be one of the best marksmen in North York in his era, so skilled, it was said, that he could hit a three-inch nail three times on the head and drive it into a board from where he was standing across a road. In the early days the only gun in use was the old flintlock musket which served as both shotgun and rifle. Shot was used to kill birds and small animals and bullets for large game.
The first log school in the Fairbank area of North York in the Eglinton-Dufferin area was built about 1825 on Dollery’s property north of Eglinton and west of Dufferin..
Dollery bought the only car in the neighborhood around 1905, early days of automobile manufacturing and ownership. He put it in his barn and practically never used it.
His first wife Sarah died in 1894. He was then fifty-nine. When he was seventy he proposed marriage to a young woman. According to North York folklore, maybe true, maybe not, he was very rich by then and she had him make a will making her the sole beneficiary before she agreed to marry him. Folklore says she tried to kill him the day after their wedding by attempting to push him over Niagara Falls where they were honeymooning so as to get the bequest right away, but she failed.
