Transitions away from car-dominance is one of the key debates in urban research, policy and practice today. Car-free public space, cycling and convenient public transport services are widely seen as desirable, yet the reconfiguration of our streets and transport networks has been incremental. This doctoral research examines how mobility in cities is governed through experiments, commonly understood as pilot projects, and whether experiments hold potential for transformative change in urban mobility systems, including transitions away from automobility. The research draws on a synthesis of sustainability transitions, transport studies and urban studies literature, and traces the outcomes of 108 experiments undertaken over two decades in two cities: Bristol (UK) and New York City (USA) between 1996/7 and 2016. The findings demonstrate that experiments can contribute to transforming the physical shape of urban mobility systems and the institutions involved in governing them, and can even contribute to transitions, if assessed as change in commuting patterns away from car use. The research compares the capacity of respective municipal governments, Bristol City Council and NYC city government for ‘transformative experimentation’, and presents an institutionalist analysis of why the transformation of Bristol’s mobility system was more limited than NYC’s. To unpack the problematisation of piecemeal, ‘project-based’ experimentation driven by competitive funding landscapes, the research compares Bristol City Council and NYC city government as two municipalities with a different degree of reliance on external funding. The stronger capacity of NYC city government can be explained by its higher degree of fiscal autonomy and mobility policy discretion, whereas Bristol City Council’s capacity was limited by the centralisation of the UK state. Yet the thesis also shows that both municipalities pursued successful endogenous strategies in response to multi-scalar structure, and points to organisational and governance practices that can create ‘political space’ for urban actors to further transitions.