This article juxtaposes the Underground Railroad with contemporary Central American smuggling practices. Activists in the US Sanctuary Movement, seeking to provide safe passage to the USA for Central American refugees, summon the legacy of the Underground Railroad as a normative frame for understanding their mission. In the original Underground Railroad, a loose network of 'conductors' ushered escaped slaves north to freedom. In contrast to immigrant rights activists and slavery abolitionists, for-profit smugglers have been vilified as violent predators. Nevertheless, surprising similarities in social practices and relationships that underpin such dramatically different cases of migration brokerage point to the contingencies, complexities and ambiguous roles of smugglers. A counterintuitive comparison between the contemporary smuggling route and the historical freedom trail shows how normative imaginaries reshape social boundaries and territorial borders in North America.