For several years this school was the only one of any note in Upper Canada; and in it and in Mr. Strachan's school at York, were educated many of those gentlemen who have filled some of the most important positions in the province. Subsequently Mr. Strachan's school was constituted the grammar school of the Eastern district. In 1806, a temporary act was passed by the Legislature and made permanent in 1808, establishing a classical and mathematical school in each of the eight districts into which Upper Canada was then divided. In the same year(1806) at the suggestion of Dr. Strachan an Act was passed, granting £400 for the purchase of apparatus for illustrating the principles of Natural Philosophy, which were to be deposited in the hands of a person employed in the instruction of youth. In 1807 an appropriation of £800 a year for four years was made to provide for the salaries of masters in the Grammar Schools to be maintained in each of the districts into which Upper Canada was divided. These masters were to be engaged by trustees appointed by the governor, and the governor's sanction was also necessary for the teacher's appointment. There is still in existence the letter, dated, April 16th, 1807, signed by Governor Gore, appointing the Rev. George Okill Stewart, D.D., Archdeacon of Kingston, first Head Master of the Home District Grammar School at York (Toronto).
North of what is now Adelaide Street (formerly Newgate Street), bounded westward by Church Street, and eastward by Jarvis Street, was a large field, almost square, containing about six acres—for many years the playground of the District Grammar School.
In the south-west corner of it, some hundred feet or more from the street boundaries, was elected the plain wooden building, about fifty-five feet long by forty wide in which, on the first Monday of June, 1807, when the population of the town was only about five hundred, the Grammar School was opened. It was attended by the sons and daughters of the well-to-do citizens of York, and on the few existing records may be found many a well known name.
In 1812, the Rev. John Strachan. D.D., was appointed Rector of York, and succeeded the Rev. Mr. Stewart as Head Master of this school.[22] Mr. Barnabas Bidwell (father of the late Hon. M. S. Bidwell) kept a good Latin School at Bath, on the Bay of Quinté, in 1811. In 1813, he removed to Kingston, where he taught for twenty years until he died in 1833.
In 1820, the "Central School at York" was opened under the mastership of Mr. Joseph Spragge, father of the late Chief Justice Spragge. Lieutenant-Governor and Lady Sarah Maitland took a special interest in the success of this school.
In a View of Upper Canada, published at Baltimore in 1814, by Mr. M. Smith, (who resided in the Province from 1808 until the breaking out of the War in 1812) he said:—
"The greater part of the inhabitants are not well educated, for, as they were poor when they came to the Province and the country being but thinly settled for a number of years, they had but little chance for the benefit of schools. But since the country has become settled, or the inhabitants rich, or in a good way of living, which is almost universally the case, they pay considerable attention to learning. Ten dollars a year is the common price given for the tuition of each scholar by good teachers."—Page 52.
In 1813, Rev. John Langhorn (a Church of England missionary at Earnestown and Bath from 1787 to 1812, and teacher of a school) made a present of his library to the inhabitants of the Bay of Quinte district. In 1814 Rev. Robert Baldwin was appointed Grammar schoolmaster at Cornwall, vice Rev. John (afterwards Dean) Bethune resigned. In 1815 the Midland District School, so-called, was incorporated.
Dr. Strachan resigned the head mastership of the District School on July 1st, 1823. He was succeeded by Mr. Samuel Armour, M.A., a graduate of Glasgow University, who afterwards became a clergyman of the English Church, and officiated many years in the township of Cavan.
The Rev. Thomas Phillips, D.D., an accomplished scholar, came out from England in 1825 to take charge of the school, and remained in the position of headmaster, much honored and beloved by his pupils, until, in 1830, chiefly by the exertions of the Governor, Sir John Colborne, Upper Canada College was established and the work of the college began in the old District Grammar School building. Classes were opened in the new buildings erected in another part of the city for the college in 1831, and the Grammar School was closed, the building being removed from its original site to the line of Nelson street (now Jarvis street), and fenced into a plot about 70 × 120 feet. The remaining portion of the six acres was handed over to Upper Canada College.