This chapter explores and explains the origins of the Underground Railroad to Canada. In 1830, Ohio’s legislature decided to implement the state’s longstanding but disused Black Laws, barring African Americans from many of the rights enjoyed by their white neighbors. Shortly thereafter, anti-black rioting in Cincinnati forced thousands of black residents to flee their homes. In response, many black Cincinnatians gathered together to explore where they might go to start their lives anew. The U.S. North? Mexico? Haiti? Liberia? Situating their decision-making process in a landscape of expanding free-soil options abroad, this chapter argues that their ultimate decision – Upper Canada – was not a foregone conclusion. By reaching out to the province’s Lieutenant Governor, they secured a promise of legal equality that not only made Canada their most enticing option, it paved the way for Canada to become the foremost international destination for fugitive slaves and free people alike.