 At Bloomfield (West Lake)

1842–1845 – Mr. Jessie H. Haines
1845–1846 – Mr. Francis Ferris
1846–1857 – Mr. Levi Varney

At Pickering Village

1878–1879 – Mr. Thomas Burgess
1879–1881 – Mr. John E. Bryant
1881–1883 – Mr. S. Percy Davis
1883–1885 – Mr. William H. Huston
1892–1905 – Mr. William P. Firth

At Newmarket

1909–1916 – Mr. William P. Firth
1927–1948 – Mr. Joseph McCulley
1948–1953 – Mr. Robert E. K. Rourke
1953–1978 – Mr. Harry M. Beer – longest serving at 25 years 
1978–1995 – Mr. Sheldon H. Clark
1995 – Mr. Peter Sturrup (acting)
1996–Present – Mr. Peter Sturrup


Pickering College is said to be haunted by the ghost of the Grey Lady, believed to be a nurse who worked in the school many years ago.The legend has been perpetuated by the occasional 'sighting', and was made popular by a now famous photograph.In the photograph, the entire staff and student body of the school is assembled for an annual school picture on the front steps of Rogers House.