[2] The roots of Pickering College trace far back into the 19th century in Bloomfield, a significant Quaker settlement near Picton at West Lake, in Prince Edward County.

There, on property (lot 13, concession 2, Military Tract) purchased by Israel Bowrman, a Quaker, a school (or seminary) was eventually established.

It is not immediately clear when the building that eventually became the West Lake Boarding School (and still stands today as a private residence) was actually erected.

For its time, the building was rather advanced in some respects, including indoor plumbing featuring a septic tank built of large red cedar logs.

According to historical sources, the school at West Lake was closed in 1865 due to lack of enrollment, partly on account of its difficult accessibility at the time.

The Act stated that it was "the opinion of the said yearly meeting of Friends that the usefulness of the said Seminary would be largely increased by changing its location to the Township of Pickering near the village of Duffins Creek".

The main school building, four storeys high in red and white brick [ref], was to be built by an Oshawa contractor for a relatively frugal sum of $24,300 (close to $475,000 in 2006 dollars).

It featured two wings that ran some 24 m (80 ft) behind the building, housing up to 75 boarding students, with the girls situated on the east side, boys on the west.

A former student, Arthur Dorland recalled later in an interview: "About the time I arrived at the school, inside plumbing had been installed and toilet accommodation had been modernized and enlarged.

This presented a serious fire hazard, for oil lamps were always liable to be knocked over, and many a glass chimney was smashed to smithereens in a pillow fight or similar fracas".

This building was done in an imposing Greek revival style with high arched windows, and a portico at the front with a roof supported by four large pillars.

The school was guided by the Friends' belief in a high standard of education that emphasized all aspects of human development – academic, spiritual and physical: "The object of Pickering College [was] to secure to its students as thorough an education as can be obtained outside of a University or of a professional school, and at the same time to surround them with all the moral influences and guarded care of a well-conducted home."

The school's emphasis on a well-rounded education included ample opportunities for rigorous exercise: ball fields, rinks and courts, and later the gymnasium surrounded the building.

The Pickering College Literary society met weekly for "musical recitals, poetry readings, discussions and debates on current issues.

An example of the trade links between school and village was a man by the name of William Peak, "who ran a "taxi service" from the Grand Trunk Railway station to the College transporting students".

Although the exact cause was never determined, it was known that the blaze began in the Principal's quarters, and, stoked by high winds, the fire quickly consumed the brick building's wooden inner frame and structure.

A debate over the future of the school ensued, with many alumni, the Village of Pickering itself (fearing a loss of business and tax revenue) and others wishing to rebuild the College on its original site.

For a time, Pickering remained the favourite; the local newspaper reported plans to rebuild the school on the same site, even larger than before, with a near doubling of capacity for boarding students.

With its larger Quaker community, direct rail link to Toronto, and the ready availability of services to the future campus, logic seemed to dictate a move there, and in 1908, sadness and objections of Alumni notwithstanding, the decision was made to relocate and rebuild the college in Newmarket.

Ruddy converted the former gymnasium into a large, lavish summer home, complete with mezzanine, four bedrooms created in part by splitting the original single storey building into two.

Local interest in restoring the former property grew steadily, but no one appeared willing or able to put forward the required $400,000 estimated cost of repair.

Nonetheless, the new building would become a Newmarket landmark, instantly recognizable; its majesty symbolic of great belief the Friends had in a solid education.

The four Romanesque columns that adorned the front of the building were eventually given the names Faith, Freedom, Friendship and Fun, to further emphasize the cornerstones of the school's philosophy and educational approach.

In 1917, an act of the Provincial Legislature transferred the assets, endowments, and property of Pickering College to an independent corporation: still primarily administered and guided by the Friends.

Under Headmaster Joseph McCulley, the school married its traditional Quaker teachings to the progressivism of John Dewey, which called for greater emphasis on problem solving and critical thinking skills rather than rote learning.

A health center is located in New House, staffed by a school nurse, who is on call 24 hours a day for the needs of boarding students.

Drawing from some of the lessons of the 1981 fire, in 1983 a brand new, three storey residence (dubbed New House) for teachers and students was constructed using a cinderblock design to render the building as fireproof as possible.

The school continues to foster athletic achievement: a mandatory after-school activity program ensures that a Pickering student receives excellent physical exercise or a way to express themselves in several different arts-related fields, as well as academic instruction.

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) 1996–2022 – Mr. Peter Sturrup 2022–Present – Dr. Cinde Lock The Pickering College ice rink is the scene of at least one film and one commercial.

Pickering College is also featured very briefly in the film The Big Hit (1998), as the high school from which Keiko Nishi (played by China Chow), is kidnapped.