When Featherstone Lake and Ellen Free Pickton Osler left their home in Falmouth, England, to live in the tiny crossroads settlement of Bond Head, Upper Canada in 1837, it was at the bequest of the Upper Canada Clergy Society, an organization that sought Anglican clergymen to minister to Canada's sparsely populated frontiers. Featherstone Osler, an Anglican priest, was given a large parish in Simcoe County, consisting of about two thousand settlers scattered over 240 square miles of mostly wild, forested land. When they arrived at Bond Head, about 65 kilometres or 40 miles north of Toronto, the Oslers thought the area quite uncivilized. By the time they moved to Dundas in 1857, they left behind them six churches, two parsonages, a Sunday school program and several public schools.

William Osler was born in the Osler parsonage at Bond Head on July 12, 1849, the eighth of Featherstone and Ellen's nine children. (The ninth died in early childhood.) Like his brothers and sisters, William attended the local school when it was in session; when no teacher could be found to teach in the remote village, he was taught at home. It was due to the erratic nature of the schooling in Bond Head that Featherstone Osler asked to be transferred to a new parish, and early in 1857 the family relocated to Dundas, Ontario, which was then a thriving city at the western end of Lake Ontario. Osler's childhood appears to have been happy but mostly unremarkable. However, while at Dundas Grammar School, he developed a taste for pranks and practical jokes that would last the rest of his life. At age fifteen, William Osler was briefly expelled from the school for shouting abuse through a keyhole at one of the headmasters. He was eventually reinstated on promise of good behaviour.

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