Throughout the 17th century, a vast majority of English settlers to the Chesapeake colonies arrived as indentured servants, trading their freedom for passage to America. About half of all white immigrants to the American colonies in the 17th and 18th centuries were indentured, with roughly 90,000 of the 120,000 emigrants to the Chesapeake arriving as bound laborers. These servants worked for a specified time, usually five to seven years, in exchange for room, board, and often a promise of land. The system fueled the early economic development of the colonies while subjecting laborers to harsh conditions and high death rates.

The experience of indentured servitude is a recurring theme in colonial American literature, offering a counterpoint to the more romanticized narratives of settlement. While less celebrated in poetry than the Pilgrim story, the struggles of indentured servants are depicted in historical fiction and the journals of the time, revealing the class tensions and exploitation inherent in the colonial project.