The chapter explores the conception of being ‘on-road’ as a gendered space, with historical antecedents. It explores the intersection of race and gender politics in early modern Britain, specifically the interwar period, which informed early youth penal reform. The analysis draws on documentary research from the Liverpool University Archives. In historicising and gendering the ‘on-road’ existence in this way, the chapter emphasises the importance of conceptual approaches expanding the explanatory scope about racialised youth’s contemporary contested positioning, beyond the customary suturing to crime and punishment. Historicising and gendering the logic of ‘the road’ enables exploration of racialised youth’s circumstances as part of a historic exclusion from the resources and opportunities associated with early modern justice reform.