This study examines how history has shaped social identity and the impacts of both on Caribbean experience in Derek Walcott’s poetry. Using New Historicism as theoretical framework, it critiques some Caribbean historical realities highlighted in the selected poems and their impacts on society at individual and societal levels with particular emphasis on identity. Four poems from different collections of Walcott are analyzed in this paper, which are “Codicil”, “The River”, “Love after Love” and “The Sea is History”. The conclusions of this critical engagement show clearly that identity in Caribbean reality is inescapably tied to the traumatic history of displacement, enslavement, migration and alienation of the Caribbean peoples.