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Detroit, the Upper Country, and the Old Northwest are often thought of as the end point to the richly textured, centuries-old Franco-Indian world, then as a key site of Indian nations’ resistance to British expansion and, later, as the precursor to competing national sovereignties between the United States and British Canada. This article explores the black experience in northern and western frontier regions from the 1750s through the 1780s to add to our understanding of this cosmopolitan place. The stature of Detroit and its vicinity relied on complex networks. The majority Native residents first forged these exchanges, later incorporating smaller numbers of European colonists and scattered imperial authorities. The unique character of what the French called the pays d’en haut and the British named the Upper Country rested on heterogeneous and interethnic networks; Detroit’s cosmopolitan residents often challenged the imperial projects that had sent them to this region in the first place. These characteristics significantly shaped the experiences of Africans in this place and time. As Indian communities and actors struggled to reassert their preeminence on the landscape and in the historical record, especially during Pontiac’s War, they opened up a new world of possibilities for enslaved and free Africans in their wake. Black individuals, as this article suggests, could widen their opportunities and, in the extreme, perhaps their status as well.