The construction of new urban roads may cause severance, or the separation of residents from local amenities or social networks. Using qualitative data from a natural experimental study, we examined severance related to a new section of urban motorway constructed through largely deprived residential neighbourhoods in Glasgow, Scotland. Semi-structured and photo-elicitation interviews were used to better understand severance and connectivity related to the new motorway, and specifically implications for individual and community-level health and well-being through active travel and social connections. Rather than a clear severance impact attributable to the motorway, a complex system of connection and severance was spoken about by participants, with the motorway being described by turns as a force for both connection and severance. We conclude that new transport infrastructure is complex, embedded, and plausibly causally related to connectedness and health. Our findings suggest the potential for a novel mechanism through which severance is enacted: the disruptive impacts that a new road may have on third places of social connection locally, even when it does not physically sever them. This supports social theories that urge a move away from conceptualising social connectedness in terms of the local neighbourhood only, towards an understanding of how we live and engage dynamically with services and people in a much wider geographical area, and may have implications for local active travel and health through changes in social connectedness.