This paper adopts a climate-conscious approach to archaeology, integrating environmental scientists’ definitions of extended droughts and megadroughts into the analysis of historical processes in the Chesapeake region of North America. We explore the relationship between drought conditions and historical processes through three case studies: Ancestral Monacans’ migration, the settlement dynamics in the Middle Potomac, and the emergence of the Powhatan chiefdom. Employing the Palmer Modified Drought Index as a paleoclimatic proxy, the research assesses how variations in rainfall and drought influenced migration, agriculture, and political formations. The findings underscore the complex interplay between Native history and environmental conditions, suggesting that the impact of climate on historical processes ranged from negligible to substantial, particularly with the adoption of maize-based agriculture. This study highlights the benefits of a climate-informed archaeological inquiry that recognizes the historically contingent ways in which climatic variability has shaped and is entangled with social change.