Graduating from the University of the West Indies in Jamaica, Walcott moved to Trinidad in 1953, working first as a teacher on various Caribbean islands and then as a journalist for the Trinidad Guardian. From 1958-59, he was in New York studying theatre and from 1959-71, he was the founding director of the Little Carib Theatre (later the Trinidad Theatre Workshop), where many of his plays were first performed. Walcott also spent part of each year in the United States, teaching at Boston University.

Walcott's plays include Ti-Jean and His Brothers (1958) and Pantomime (1978), but most critics consider his finest dramatic work to be Dream on Monkey Mountain (1967), which was originally commissioned by the Royal Shakespeare Company. His plays are typically embedded in folk tradition and history, and combine verse, prose, song, dance and calypso rhythms.

However, Walcott is best known for his poetry, first achieving recognition in 1962 with his highly acclaimed collection, In a Green Night: Poems 1948-1960. This celebrates the natural beauty of the Caribbean landscape and also establishes the poet's aim of creating a literature truthful to West Indian life. Another Life (1973) has been described as "one of the best long autobiographical poems in English". The Star-Apple Kingdom (1979) uses terser language to explore linguistic and racial divisions in Caribbean culture. The Castaway (1965) and The Gulf (1969) reveal in their titles Walcott's feelings of alienation as he tries to balance his European cultural orientation with the black and Creole folk cultures of his native Caribbean. The Fortunate Traveller (1981) and Midsummer (1984) examine Walcott's experience and feelings of exile as a black writer in the United States.