John Small

Names such as Simcoe, Jarvis, Shank and Shaw are all well known as being those of some of the Queen’s Rangers officers who led the Regiment during its duties constructing the town of York.  There is another officer, however, who is lesser known today but who was a force to be reckoned with in his day.  His name was John Small.


Born in Cirencester, England in 1746, he was the son of a haberdasher who rose considerably above his original station.  How and when he joined the Queen’s Rangers is unclear, but it seems that he did not fight with the Regiment during the Revolution.  In 1792 he was appointed as the Clerk of the Executive Council of Upper Canada through the intercession of British Home Secretary Henry Dundas, and sailed to the colony at the same time as John Graves Simcoe to take up his post.  He is also noted at the same time as having been commissioned as a Lieutenant in the Queen’s Rangers.

The main business of the Executive Council at the time, which met as infrequently as once a year, was to confirm land grants and sales to Loyalists and others settling in York.  Many of the official documents from this period are signed by John Small.

This position, though a significant one in the early colony, paid a mere £100 a year, which was little more than the wage of a manual labourer.  John Small perhaps felt insecure in his position in society. Simcoe described Small in his memoirs as “a Gentleman who possesses and is entitled to my highest confidence,” but many other descriptions from the period suggest that he was lazy, self-serving and inefficient.

John Small was able, through his position, to purchase 2,500 desirable acres of land and to resell them to later settlers at a profit.  This land speculation allowed him to amass a sizeable fortune, as well as to secure two desirable properties for himself in the colony – a “city” lot on which already existed one of the first permanent buildings in the settlement, as well as a 100 acre “country” lot to the east of York, which he could further develop.

The one acre city lot was located at the south eastern corner of what are today Berkeley and Front streets.  A log cabin build by a carpenter from whom he purchased the lot, the house was grandly named Berkeley Castle.  The street took its name from the house many years later.  Expanded by his children, covered in stucco and Georgian decoration, it stood until it was finally torn down in 1925.  Although it had been the social hub of the early town of York, by the time that it was demolished it was surrounded by industrial buildings and was in considerable disrepair.

The country lot that he purchased was roughly bounded by the modern streets of Queen, Coxwell, Danforth and Woodbine.  Whether by accident or design, the road built by the Queen’s Rangers from York to Kingston took a considerable detour through John Small’s plot, following roughly the course of what is now Kingston Road.  Along this road, cleared at no expense to himself, John Small sub-let smaller plots to create a small village centred on several farms, a sawmill and at least one inn that provided entertainment and lodging for farmers on their way to market in York.  He appears to have also run a private toll booth on the road near the intersection of Kingston Road and Queen Street, charging a fee for the route’s upkeep.  Although he named this settlement Berkeley, the inhabitants preferred the name Norway, after the type of pine trees prevalent in the area.  Vestiges of this name are found today in both St John Norway Anglican Church (built by one of John Small’s descendants) as well as Norway Public School.

By early 20th century, this area was still not within the bounds of the city proper, and much of it was taken up by the Toronto Golf Club, the third oldest golf club in North America.  A major feature of the course was a body of water known as “Small’s Pond.”  The club sold the land to developers in 1913, who quickly built houses that could be serviced by the street car line that the city was extending along Queen and Gerrard Streets.  Gerrard, which had previously stopped at Coxwell, was pushed further eastward to reach Main Street, using the route of a foot path across the golf course that led to the Club House.  This created the gap in Gerrard Street as it crosses Coxwell that still exists today

Small’s Pond became polluted over time from the encroachment of houses around its perimeters, and by the 1930s, residents complained to the city about the noxious odours coming from it.  The city filled in the pond, the outline of which can still be seen in the form of two city parks, and drove Dundas street across its middle to link up with Kingston Road.

Small used his wealth to obtain social status, becoming a Justice of the Peace for York in 1796, and a Lieutenant Colonel in the York Militia in 1798.  John Small is perhaps most famous, however, for having fought a duel stemming from comments made by another prominent citizen of the settlement during a Christmas celebration in 1799. 

Small’s wife, Elizabeth, had publicly quarreled at some point with the Marianne White, the wife of Attorney General John White.  In turn, at a Christmas Party in 1799, White made the public accusation that Elizabeth Small lacked “moral fibre and marital fidelity.”  He claimed that she had been the former mistress of a British Lord, the Fifth Earl of Berkeley, who had paid John Small to spirit her away to the colonies when he had tired of her.  There was also the suggestion that John White could speak authoritatively about her infidelity as he had himself been sleeping with her.

In any case, Small took umbrage with White, and challenged him to a duel.  The duel, with pistols, took place on 3 January, 1800.  White was struck in the hip and mortally wounded, though he lingered for several days before succumbing to the wound.  Small was charged with murder, but as was the practice in the period, he was acquitted of murder after a brief trial because the duel was conducted in a “fair” manner.

This incident, however, made Small somewhat of a social pariah within Upper Canada, though he remained as the Clerk for the Executive Council until his death.  When he stood for election to the House of Assembly in 1800, and despite his standing as a wealthy member of the community, he was defeated soundly.  He also failed to be elected when he made a second attempt a year later.

While John Small was not a popular member of either the Regiment or Upper Canadian society, there can be no doubt that he made his mark on the early settlement at York.