This article provides an in-depth cultural study England’s urban middling sort—those in between wage labourers and the gentry—at the beginning of the seventeenth century, by concentrating on one community in a major street in Bristol. This demographic has long been of interest to historians looking to understand the major social changes of the early modern period, but little is known about the total urban experience of these individuals in these pre-Restoration years: the way their creative and entertainment pursuits connected with their commercial, domestic, and local political responsibilities. Bristol’s Wine Street represents a concentration of such figures within a middling enclave characterised by commercialised leisure services, luxury craft goods, and favourable political environments. This article shows how the middling “play” sustained by these enclaves shaped the early modern city. Wine Street was home to goldsmiths’ standings and shops, instrument-makers, inn-holding widows, aldermen, mayors, and the longest-running playhouse of early modern England outside of London—a venue run by Nicholas and Margaret Woolfe. The Woolfes and their neighbours demonstrate how urban middling status is bound up with “play” and in turn both complicated and defined by neighbourhood, marriage, widowhood, and inheritance. The interrelated individuals and institutions of Wine Street reveal crucial connections between creativity, skill, and enterprise and indicate their centrality to the social changes of the late sixteenth and early seventeenth centuries.