The analysis in this chapter draws on documentary research from the Liverpool University Archives, including the Fletcher Report (1930) and the digitized catalogue of the Eugenics Review, a populist journal spanning 1909 to 1968. While documents like the Report introduced racialized youth to Britain, as a problematic cohort, the pseudo-science promulgated in the Review supported the racial politics positioning these youth outside the redemptive scope of early penal reform efforts. Fletcher (1930: 26) concluded that ‘These families have a low standard of life, morally and economically, and there appears to be little future for the children.’ This conclusion stands counter to narratives supporting rehabilitation for White, working class youth, especially during the interwar period (Miller, 2022). In this chapter, the concept of being on ‘the road’ offers a unique lens to give gendered relevance to this history. For example, during this time, young women’s search for opportunities met with resistance at both the societal and institutional levels. In this regard, Crenshaw’s intersectional logic attends to the important intersections of race, gender, youth giving critical currency to the wider implications of this exclusion. In Historicising and gendering ‘on road’ in this way, the chapter emphasizes the importance of conceptual approaches expanding the explanatory scope about racialized youth’s contemporary contested positioning, beyond the customary malignant to suturing to crime and punishment.