Each summer, a ‘perpetual fair’ plagued eighteenth-century London, a city in transition overrun by a burgeoning population. City officials attempted to control disorderly urban amusement according to their own gendered understandings of order and morality. Frequently derided as locations of dangerous femininity disrupting masculine commerce, fairs withstood regulation attempts. Fairs were important in the lives of ordinary Londoners as sites of women’s work, sociability, and local and national identity formation. Rarely studied as vital to London’s modernisation, urban fairs are a microcosm of London’s transforming society, demonstrating how metropolitan changes were popularly contested. This study contributes to our understanding of popular culture and modernisation in Britain during the formative years of its global empire. Fascinating examples drawn from literary and visual culture make this an engaging study for scholars and students of late Stuart and early Georgian Britain, urban and gender history, World’s Fairs and cultural studies.