The history of St. Gregory Catholic school is rich with legends, stories and some mystery. Many of the facts surrounding the school’s history can be learned only by talking to the local amateur historians and parishioners. The Prince Edward Historical Society provides interesting documentation as does Ed Buckley’s book, The Parish of St. Michael the Archangel, 1829-1993
In 1828, the land on which the church and school were eventually built, was donated from the private holdings of the Anglican minister at that time, named Rev. William Macauley. Father William Fraser was the Catholic priest from St. Michael’s parish in Belleville who negotiated for the land with Rev. William Macauley. (Speculation abounds as to the origins, therefore, of the name” St. William” for the church). There is evidence to suggest that some form of Catholic School was operating in Picton as early as 1836, probably using the church building.
According to a table dated Toronto, April 30th, 1855, the only school in the Prince Edward County was a formally registered Catholic School in operation in Picton ( Hallowell) dating from 1854. The local residents and Prince Edward County archivists believe that the school was a wooden frame one-room school house on the site of what is now St. Gregory Catholic School. It was probably known as St. William school, since the church which existed beside it was named St. William.