The Sierra Maestra is a mountain range that runs westward across the south of the old Oriente Province in southeast Cuba, rising abruptly from the coast.

[1] Some view it as a series of connecting ranges (Vela, Santa Catalina, Quemado Grande, Daña Mariana),[2] which join with others to the west.

After Fidel Castro returned to Cuba in 1956 from exile in Mexico, he and the few other survivors from the failed 1953 attack on Moncada Barracks hid in the Sierra Maestra.

They built up guerrilla columns, and in collaboration with other groups in the central provinces, Escopeteros on the foot-hills and plains, and the urban resistance, eventually overthrew Batista on 1 January 1959.

Calls of the Cuban subspecies of the ivory-billed woodpecker, now possibly extinct, were reported but not confirmed in the Sierra Maestra in 1998; it remains the most likely habitat to contain a population of the species.