V. S. Naipaul’s autobiographical novel, The Enigma of Arrival, presents a first person narrative of postcolonial migration told by a middle-aged Indian writer who leaves his homeland Trinidad for England at the age of eighteen and later takes up residence in a manorial cottage on the grounds of a Victorian-Edwardian country estate in Wiltshire. Many readers of The Enigma of Arrival have voiced discomfort, locating in the novel Naipaul’s emotional investment in deep old England and his sense of wrongness in postimperial England. The sense of belatedness and wrongness pervasive in the novel, however, does not necessarily mean a politically reactionary position occupied by a conservative essentialist who pines for authentic England and Englishness. This paper aims to acknowledge an idiosyncratic narrative of Naipaul’s postcolonial migration that heavily draws on the localist discourse of Englishness and analyze Naipaul’s landscape aesthetics. Naipaul implicates his novel in the profound sense of melancholia that his narrator experiences in the process of postcolonial dislocation. Melancholia on Naipaul’s part, however, is not a simple retrograde vision of colonial desire but a crucial means of coming to terms with the enigmatic process of departure and arrival that a postcolonial subject experiences. For the melancholia pervasive in The Enigma of Arrival is sparked and shaped by specific cultural concerns and struggles conditioned and framed by postcolonial modernity, thus serving as a paradigm symptomatic of postcolonial modernity that Naipaul’s novel attempts to capture.