Archaeologists and anthropologists have long been interested in the study of past human interaction. In the Indo-Pacific, research has focused on the age and processes by which islands were settled and the role that intermediary communities played in these histories. Torres Strait, on Australia’s northern border, represents one such frontier zone. For millennia this 48,000 km2 area (containing at least 274 islands) separated predominately horticultural and pottery-using Melanesians and hunter-gatherer Australians, a contrast considered by some to be ‘starker and more perplexingly than anywhere else in the world’ (Walker 1972:405). Mirroring archaeological explanations and theoretical interests elsewhere, Coral Sea chronicles have transitioned between those prioritising large-scale migration to narratives of entanglement on the periphery of ancient globalisations. This paper develops the theme of entanglement, exploring distinctive regionally diverging histories of innovation and interaction occurring in Western, Central and Eastern Torres Strait. We suggest that traditional histories, involving the wandering trackways of Culture Heroes, provide useful insights into the deep history of human interactions, thereby helping us to understand patterns observed in the archaeological and linguistic record.