This article investigates interventions in the gutter play of British working class children in the first decade of the 20th century through their re-location within Free Kindergartens. In contemporary literature, the street child was viewed through a binary lens, as both ‘at risk’ and ‘as risk’, reflecting wider societal discourses in a period of rapidly developing social policy. The paper interrogates the motivations of free kindergarten activists from the standpoint of a range of theory and builds on recent papers discussing 21st century urban childhoods. The findings suggest both historical continuities and discontinuities in the theorisation of risk, which have implications for current social policy, urban design and early childhood education. The questions raised include issues of children’s rights, citizenship, inclusion and cultural diversity.