This paper examines and analyzes Kipling's representation of colonial Calcutta in his travel sketch, The City of Dreadful Night. It explores the role of the European gaze at length seeking to uncover the ways in which it became complicit in delineating not only the colonial space but also the (hitherto more secure) notion of Englishness. In order to do so, this paper exploits Freud's play on the concepts of heimlich and unheimlich, shining a light on how the colonial space, in Kipling's imperial narrative, functioned as a covert force in the formulation of identities. © Rupkatha Journal on Interdisciplinary Studies in Humanities.