The number of slaves in Upper Canada was also diminished by what seems at first sight paradoxical, that is, their flight across the Detroit River into American territory. So long as Detroit and its vicinity were British in fact and even for some years later, Section 6 of the Ordinance of 1787 "that there shall be neither slavery nor involuntary servitude in the said territory otherwise than as punishment of crime" was a dead letter: but when Michigan was incorporated as a territory in 1805, the Ordinance of 1787 became legally and at least in form effective. Many slaves made their way from Canada to Detroit, then a real land of the free; so many, indeed, that we find that a company of Negro militia composed entirely of escaped slaves from Canada was formed in Detroit in 1806 to assist in the general defence of the territory.[14]

The number of slaves in Upper Canada cannot be ascertained with anything approaching accuracy. The returns of the census of 1784 show that very many of the 212 slaves in the District of Montreal, which then extended from the Rivers St. Maurice and Godfrey to the Detroit River de jure and to the Mississippi de facto, were the property of the United Empire Loyalists on the St. Lawrence in territory which in 1791 became part of the new Province of Upper Canada.

The settlement crept up the St. Lawrence and Lake Ontario so as to be as far as the River Trent by the end of the eighteenth century: and Prince Edward County had also its quota of settlers. Until the nineteenth century had set in there were practically no settlers from the Trent to near York (Toronto) but that splendid territory of level clay and loam land covered by magnificent forests of beech and maple gradually filled in and by the 30's was fairly well settled. In the latter territory there were very few, if any, slaves.[15]

Farther east, however, in what became the Eastern and Midland Districts there were many slaves. It is probable that by far the greatest number had their habitat in that region. When York became the provincial capital (1796-7) slaves were brought to that place by their masters. In the Niagara region there were also some slaves, in great part bought from the Six Nation Indians as some of these in the eastern part of the province were bought from the Mississaguas who had a rendezvous on Carleton Island near Kingston. In the Detroit region there were many slaves, some of them Panis;[16] and many of both kinds, Panis and Negro bought from the Shawanese, Pottawattaimies and other Western Indians, taken for the most part from the Ohio and Kentucky country. Most of these slaves were west of the river, few being in the Province of Upper Canada de jure. Omitting Detroit, the number of slaves in the province at the time of the Act of 1793 was probably not far from 500.[17]

In the Eastern District, part of which became the District of Johntown in 1798, there were certainly some slaves. Justus Sherwood one of the first settlers brought a Negro slave Caesar Congo to his location near Prescott. Caesar was afterwards sold to a half pay officer Captain Bottom settled about six miles above Prescott and after about twenty years service was emancipated by his master. Caesar afterwards married a woman of color and lived in Brockville for many years and until his death. Daniel Jones another old settler had a female Negro slave and there were a few more slaves in the district.[18]

It is possible that this part of the province was the home of a Negro who at the age of 101 appeared at the Assize Court at Ottawa in 1867 to give evidence. He was born in the Colony of New York in 1766, had been brought to Upper Canada by his master, a United Empire Loyalist, had fought through the war of 1812 on the British side, was present at the Battles of Chippewa and Lundy's Lane and was wounded at Sackett's Harbor.[19]

In the Midland District at Kingston such leading families as the Cartwrights, Herkimers and Everetts were slave owners. Further west the Ruttans, Bogarts, Van Alstynes,[20] Petersons, Allens, Clarks, Bowers, Thompsons, Meyers, Spencers, Perrys, Pruyns, speaking generally all the people of substance had their slaves.[21]