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In the first half of the seventeenth century, English boosters of settlement in the Chesapeake colonies promoted the region as a land of abundance rich with agricultural, forest, and mineral resources. While historians have focused on tobacco cultivation as a primary factor in the development of the region’s economy, settlement patterns, and adoption of indentured and enslaved labor, early colonial planners and English officials were initially intrigued by the region’s forest resources and its potential to supply England’s expanding naval forces and alleviate timber shortages at home. While shipping costs and chronic labor shortages prevented the fulfillment of imperial plans to capitalize on the forests of the Chesapeake in the mid-seventeenth century, colonial settlers continued interacting with the region’s forests in different ways as they cleared land for cultivation and also turned to remaining wood lots for income. Examining a combination of colonial promotional tracts, colonial laws, and judicial cases, this study uses the concept of political ecology to explain the multiple factors that shaped and limited land use in the Chesapeake and ultimately connected the region to larger Atlantic World economies by 1700. The political ecology of settler colonial Chesapeake societies involved a multilayered set of local and imperial practices and regulations that adapted to the realities of variable soil quality, adjusted to Atlantic World demand for timber products, and transformed the forests of the region, altering the landscape in profound, long-term ways.