This chapter explores highly publicized episodes of international free-soil border crossing by land and by sea in the 1830s and 1840s. It was during these decades that the so-called Underground Railroad to Canada became a recognizable feature of the American anti-slavery landscape. Anti-slavery advocates publicly and volubly celebrated each instance of former slaves escaping the reach of slave-holders, and the publicity generated by border-crossing slaves inspired abolitionists to see Canada as a beacon of black freedom. Cumulatively, the successful escape of fugitive slaves to Canada, Mexico, and the British West Indies also catalyzed international diplomatic crises that permanently altered the geopolitical map of slavery and freedom. While millions remained enslaved during the antebellum era, the efforts of fugitive slaves to claim their freedom transformed international free-soil havens into powerful symbols of freedom and escape.