My dissertation is a social and environmental history of the woodlands that stretch from Campeche, southwest to the Laguna de Términos, and south to the Petén of Guatemala. Today, this area is a marginal, forgotten borderland between Mexico and Guatemala, but I demonstrate that this has not always been so. Historical processes controlled by non-elite and indigenous people during the sixteenth and seventeenth centuries—which I explicate using archival manuscript material in Spanish and English, correlated with environmental and archaeological data—created a powerful, contested space, which Spain was never able to fully control. These same processes also caused the erasure of the forests in southern Yucatan and northern Guatemala from public memory. By focusing on the use, exchange, conceptualization, and globalization of local ecologies, I argue that the forests connected a diverse array of Spanish, English, and Maya communities by facilitating a multitude of quotidian transcultural and transimperial interactions. These connections afforded non-elites power to build alternative communities that helped them navigate their colonial and arboreal worlds. Rather than keeping people divided, forests wove vast networks of exchange, meaning, and power, which warped the larger early modern societies around them. Thus, my dissertation reveals that ecologies, empires, and indigenous-dominated borderlands were not separated by difficult geography, but were actually deeply entangled from the bottom up by local, everyday environmental interactions. The effects of such contested connections rippled outward from the Peninsula to transform the early modern world.