Oliver Prentice of Pittstown: From New York to Upper Canada and Back

PrenticeNet, a genealogical website dedicated to tracing all things Prentice, Prentiss, Prentis, and related name variants across the world, hosts a detailed and thoroughly researched biography of Oliver Prentice — a man whose story begins in Pittstown, New York, and takes some remarkable turns across two countries and a war.

Oliver Prentice came to Upper Canada from Rensselaer County, New York, in 1801, with his wife Lydia Delong and two children. Oliver and Lydia had been married on 16 November 1796 at Pittstown, with the marriage record appearing in a "badly water-stained notebook," the account book and ledger of Simeon Button, justice of the peace and merchant. The couple would go on to have twelve children in total — four born in the United States and eight in Upper Canada. prenticenet

Oliver established himself as a landowner in what is now the greater Toronto area, acquiring and selling lots in both Markham Township and Etobicoke. But the most dramatic chapter of his life came during the War of 1812. In 1813, a Jacob Anderson accused Oliver of treason, claiming that Oliver had tried to persuade him to desert to the enemy and carry papers across for fifteen dollars and a horse. Oliver was subsequently charged with high treason by the legislature of Upper Canada.

As a result of this charge, Oliver moved his family to Ohio, sometime before 1815 — a considerable undertaking, with his wife possibly pregnant and seven children in tow. The family appears to have returned to Upper Canada by around 1818, settling once again on their lot in Etobicoke. prenticenet

Oliver is last recorded as a landholder in an 1837 Toronto directory, and appears to have died sometime between 1841 and 1846. The biography, written by David Phillips and published on PrenticeNet in 2018, is a vivid piece of genealogical detective work anchored firmly in Pittstown's history.