In the next twenty years, urban populations in Africa are expected to double, while urban land cover could triple. An often-overlooked dimension of this urban transformation is the growth of small towns and medium-sized cities. In this paper, we explore the ways in which small towns are straddling rural and urban life, and consider how insights into this in-betweenness can contribute to our understanding of Africa’s urban transformation. In particular, we examine the ways in which urbanism is produced and expressed in places where urban living is emerging but the administrative label for such locations is still ‘village’. For this purpose, we draw on case-study material from two small towns in Tanzania, comprising both qualitative and quantitative data, including analyses of photographs and maps collected in 2010–2018. First, we explore the dwindling role of agriculture and the importance of farming, businesses and services for the diversification of livelihoods. However, income diversification varies substantially among population groups, depending on economic and migrant status, gender, and age. Second, we show the ways in which institutions, buildings, and transport infrastructure display the material dimensions of urbanism, and how urbanism is planned and aspired to. Third, we describe how well-established middle-aged households, independent women (some of whom are mothers), and young people, mostly living in single-person households, explain their visions and values of the ways in which urbanism is expressed in small towns. In conclusion, we discuss the implications of this urban life-in-becoming of small towns for urban planning, emphasizing the importance of the development of inclusive local governance. Ultimately, we argue that our study establishes an important starting point for further explorations of the role of the simultaneous production and expression of urbanism in small town urbanization.