This article provides an in-depth cultural study of England’s urban middling sort—those in-between wage labourers and the gentry—at the beginning of the seventeenth century, concentrating on one community in a major street in Bristol. This demographic has long been of interest to historians seeking to understand the major social changes of the early modern period, but little is known about the total urban experience of such individuals prior to the Restoration. Wine Street was home to goldsmiths’ standings and shops, instrument-makers, inn-holding widows, aldermen, mayors, and one of the longest-running playhouses in early modern England outside of London—a venue run by Nicholas and Margaret Woolfe. This study seeks to understand more about the everyday lives of this crucial demographic through a holistic micro-history of one particular community—grounding them in a specific place and time and providing an earlier case-study than is generally available in existing literature. Doing so demonstrates how middling status was complicated and defined by neighbourhood, marriage, widowhood, and inheritance. More widely, this group of Wine Street tradespeople, artisans and proprietors lived in a location that was in large part distinguished by forms of ‘play’, the elastic early modern term used here to refer to various forms of commercial recreation, from drama to inn-going to luxury shopping. I establish how, in such urban environments, middling status can be distinctly recognised in the imbrication of play with cultural and commercial identity.

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This article recognizes the significance of commercial entertainment producers in early modern England operating outside of London. In doing so, it offers fresh methodological approaches for understanding pre-modern social status. I explore the geographical and social places of independent bearwards – individuals who kept bears for the commercial sport of baiting. Regional figures involved in entertainment production have been little explored and left behind frustratingly few biographical details. Yet three generations of one family – the Whitestones of Ormskirk in Lancashire (1610s through the 1630s) – do leave substantial surviving documentary evidence about their activities, assets, and networks. I use the Whitestones's probate inventories and wills and their and their neighbours’ court depositions and petitions to offer for the first time a holistic appraisal of the material, economic, and cultural circumstances of the bearward. By stepping inside the households and communities of several generations of independent entertainment producers, we can appreciate their complex and variable social status and the role of commercial recreation in social mobility. I finish by considering the human–animal relationships that underpinned the bearward's place in early modern England, offering fresh evidence of bears’ living arrangements and a theoretical framework for discussing their exploitation in the blood sport industry.

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