This study explores how illicit transatlantic trade relations with the Dutch in seventeenth-century Virginia can be identified through the material record. The research was motivated by recent excavations at a seventeenth-century plantation on Virginia’s Eastern Shore. Eyreville, as it is now known, was a hub of transatlantic trade during the formative years of the Virginia colony. The recognizable presence of Dutch trade goods, coupled with the site’s pro-Dutch merchant residents, prompted the investigation into material signatures of illicit trade on the Eastern Shore and the Chesapeake. The identification of these material signatures is based on extensive research into geopolitical histories, trade networks, the production and distribution of trade goods, and archaeological evidence. This is achieved through the lens of network analysis and structuration theory. Combined with a rich documentary record, archaeological and artifactual analysis illuminates the effects of European globalization, specifically conflicts such as the War of Three Kingdoms from 1642-1649, and regulations such as those imposed through the British Navigation Acts and by the Dutch West India Company. Considering the complexity of this historical context and the modes of analysis involved, a multiscalar approach/perspective is key to discerning how these trade relations occurred.