This contribution uses the terms “territoriality” and “legal spatiality” to consider how they shape our understanding of the significance of the North American border between the US and Canada (British North America) in the nineteenth century. It looks, first, at the ways in which Black intellectual leaders constructed Upper Canada as a counterterritory to the United States in the context of debating Black emigration by combining politics and geography to challenge conflicting territorialities. Canada’s ambiguous position as a safe haven under the British lion’s paw that was formerly invested in slavery and the slave trade is reinforced, second, by the increasing numbers of black fugitives onto its territories. This perceived mass exodus provoked aggressive reactions from US slaveholders who relied on the fugitive slave laws to lay claims on their “property” in the form of fugitive slave extradition cases. The activism by Black communities along the border that emerged from the crises to save fugitives from being returned to bondage, this contribution shows, enacted a form of counterterritoriality that called on the British imperial center to challenge the legality of slavery, introducing alternative forms of “legal spatiality.”