On the basis of an emerging reassessment of the medieval urban experience in southern Wales, this article seeks to challenge the predominant view of Wales as being overwhelmingly rural before the nineteenth century. The study of Welsh towns has been limited by the survival of sources that in other regions have generated a renewed interest in the study of medieval urban society. Employing unusual sources that are available, generalizations are made here from the findings of case studies of two towns, Haverfordwest and Chepstow, in order to contribute to a regional synthesis of the urban experience in southern Wales. From this regional synthesis it will be possible to compare urban society in late medieval southern Wales with other regions in Britain and Europe in order to determine its particular characteristics, and with implications for later developments.