This chapter presents a case study of Mexican city of Matamoros, Tamaulipas that offers several profound insights, especially when comparing the city and its cycling community to its transborder neighbor. Matamoros lies 30 km west of the Gulf of Mexico and directly underneath la frontera of the United States, sharing three international bridges with Brownsville, Texas. Organizers of the cycling collective Doble Rueda rotate through in reflective vests, graciously "plugging" intersections against passing cars to keep the group flowing through potholed city streets with no cycling infrastructure. The chapter explores how Doble Rueda uses the bicycle as a means to free space and activities from the many delimitations within the troubled city. It demonstrates how bicycle dependent riders are creating spaces of freedom and empowerment within a difficult social and political context. Residents describe the bicycle to be the safest form of mobility in Matamoros. "Aburrido" is the Rueda's unofficial slogan as they ride in their festive transportation celebrations.