This study provides a new perspective on civil society in Cuba during the nineteenth century based on concrete information about multiple types of association in different regions of the island. Modern associations developed mainly to meet specific social and cultural needs, achieve legal autonomy from the state and exercise free association despite colonial constraints. This long-term evolution covers several periods of intersections between civil society and political spheres, framed primarily by non-violent constitutionalist and reformist struggles rather than armed separatist conflicts. These findings contradict prevalent interpretations that portray an endemically weak yet increasingly militant civil society. Instead, a growing, moderate, and progressively autonomous and diverse civil society contributed gradually to undermine colonial despotism and establish key bases for post-independence democracy.