This article focuses on the distinctive modes of urban spectatorship Thomas De Quincey adopts in his autobiographical Confessions of an English Opium-Eater (1821). In keeping with De Quincey’s tendency to pastoralize his childhood, Part I of Confessions presents a young man who initially walks and reads London as if it were a village, unwilling, or perhaps unable, to register the cityscape. In these passages, which correspond to his first, 1802–1803 residence in London, De Quincey embodies a recognizably Wordsworthian subjectivity and a recognizably peripatetic perspective. Through a careful reconstruction of his younger self as an urban peripatetic, De Quincey reveals the insufficiency of a rural subjectivity to modernity and the metropolis, and examining Confessions in these terms provides new insight into De Quincey’s richly ambivalent relationship with Wordsworth and The Prelude. When De Quincey depicts his second (1804) stay in London in Part II of Confessions, he depicts a younger self now able to digest – and, one might say, to artistically and sympathetically exploit – the city. In this mode, De Quincey may be properly understood as the earliest flâneur; with characteristic prescience, moreover, De Quincey anticipates the limits of flânerie that Charles Baudelaire would eventually come to register and that Walter Benjamin later described and theorized. In depicting the self as urban peripatetic and (proto-)flâneur, De Quincey’s Confessions marks a key moment in the history of modern urban spectatorship and practices of walking, constituting a provocative early attempt at negotiating the relationships between the eye and the crowd, the body and the pavement, the self and the modern metropolis.