The first chapter examines the changing landscape of slavery and freedom that developed in North America in the revolutionary era. It explores how and why opportunities for enslaved people to permanently escape bondage expanded significantly between the colonial era and the early nineteenth century. The chapter begins with a discussion of how slave flight was characterized during the colonial period, underscoring the informal nature of sancturary spaces and the lack of any spaces of "formal freedom" throughout the continent, as slavery was legally sanctioned everywhere. It then delves into the major transitions that occurred in the Age of Revolutions, with the abolition of slavery in the Northern United States, British Canada, and Mexico; as well as the wave of manumissions in the southern states that greatly bolstered urban free black communities. By the mid-1830s, enslaved people who found themselves trapped in the second slavery of the American South saw potential "spaces of freedom" in every direction: informal freedom within urban areas in the South itself; semi-formal (contested) freedom in the Northern United States; and formal freedom beyond the borders of the United States.