This book argues that repeated waves of frustrated urban development in the colonial Chesapeake region were critical to framing the political and economic structures of the region’s plantation society. Although the early Chesapeake never boasted major cities, intense debates over the spaces, processes, and consequences of urbanization between imperial officials, English merchants, and colonial factions persisted over two centuries. This was because, rather than being simply the product of deterministic geographic, social, and economic forces, towns and cities were institutional and legal forms of colonial space that were consciously crafted by colonists and officials in the struggle to define the nature of early modern empire. Exploring these contests reveals long-overlooked ways in which important questions about the imperial constitution and mercantilism were negotiated by ordinary people through the quotidian production of such spaces. The book demonstrates that the development of the rural tobacco plantation system, defined by the exploitation of enslaved labor on large estates by a well-connected imperial oligarchy, was a result of this process; it was not inevitable, but was honed in response to repeated efforts to reshape and redefine the economic, institutional, and political spaces of the Chesapeake. The book argues that these struggles were a crucial catalyst in the formation of a distinctive planter vision of civic order and imperial political economy that continued to shape southern planters’ agrarian republicanism after the American Revolution.