School routes are paths where children learn, gain independence, forge their identity and interact with other beings – be they human or non-human. Many aspects that determine this journey are of social and cultural nature. But the spatial shaping of the way to school can also prove very significant. When it comes to the formalisation of school routes in urban environments, attention is generally focused on guaranteeing children’s safety from traffic, at a planning level. This chapter argues that many design aspects also need to be considered to contribute to making this journey not only safe but also enriching and playful. Should the school journey be considered as ‘a third place’ (Oldenburg 1989/1999), it needs to be carefully conceived in its smallest details. Through decisions regarding metrics, spatial divisions, paving, vegetation, lighting features, urban furniture, building entrances and ground floors, private property edges, city spatial designers – mainly architects, landscape architects and urban designers – can have a radical impact on the way children, and people in general, might experience these routes. Whether conscious or unconscious, every design decision will have a direct effect on future appropriation, by supporting (or impeding) some activities. Rather than promoting specific solutions, design toolkits or absolute answers, this chapter is an invitation for practitioners to question their design decisions, through the lens of child friendliness and more specifically along the concept of ‘learning on the way’. Admittedly, it is rather explorative than assertive.