In his autofictional essay ‘Night Walks’ (1860), Charles Dickens grapples with insomnia by chronicling his restless wanderings through nocturnal London. Nocturnal darkness, the essay suggests, can extend its shrouding properties to those who wander through it, inhibiting both the ability to see others and to be seen by them. Physical darkness is thus intertwined with epistemological darkness, its veiling abilities both produce and are fortified by the illegible opacity of the encounter between Dickens and the people of the city. The present chapter seeks to complicate the notion of an urban darkness as a mere atmospheric stylistic device for Gothic mysteries or transgressive adventures. It suggests reading the nocturnal city not merely as a foil of the walker’s troubled psyche, but as an agent which resists bourgeois practices of exploring and writing to bring about order. By providing a close reading of the essay’s engagement with practices of nocturnal straying, it aims to examine the position of the subject within the sleepless cityscape. Principally, the intricate relationship between physical darkness, the limitations of hermeneutical resources of the wandering middle-class journalist and its implications for the perception of Self, Other and space will be explored.