This dissertation presents a decolonial overview of handed-down music practices commonly framed as heritage in Northern Colombia, and follows the question of how intergenerational acts of musical transmission take place. As heritage, the music practices under scrutiny, such as cumbia, lumbalú, porro, bailes cantaos, vallenato, and champeta, connect past and present in a temporal articulation that assumes cultural transmission has been achieved. However, these practices are affected by gaps, erasures, and mistranslations proper of colonial/modern entanglements. Caribbean Palimpsests interrogates issues of colonial/subaltern difference in the Americas, while documenting decolonial reconstitutions pulled by music practices in the spheres of space, time and being, which disturb the modern/colonial/extractivist political arrangement reproducing in the Caribbean since Columbus’ arrival at La Hispaniola island in the late fifteenth century. As I demonstrate, palimpsests exemplify how extended processes of political, musical and cultural replication are carried out, particularly in postcolonial contexts. The intermittent occurrence of inscriptions in palimpsests, their seeming invisibility coming under question on closer inspection, account for the gaps and erasures that characterise colonial trajectories, where collective memory and culturally specific knowledge—musical or otherwise—are primarily passed on and reproduced through embodied performance. This work argues that the reproduction of intergenerationally transmitted musical forms follows a palimpsestic and trans-temporal trajectory that is audible at times, and silenced at others. Across Caribbean modernity, the irregular and yet rhythmic re-surfacing of these forms of music-making constantly rework the mythical and sonic elements of the colonial Caribbean society.