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World’s megacities are facing acute sustainability challenges. Persistent problems such as urban pollution, resource depletion, climate change, poverty and social inequalities are shaping unsustainable futures for some of the world’s most populated regions. How can these challenges be tackled? Focusing on the urban mobility regimes that contribute to the acute challenges, this thesis investigates if they can transition toward sustainability. According to sustainability transitions studies, experimentation is vital for making such a transition, through replacing existing unsustainable socio-technical regimes such as fossil fuel-based automobility. Besides niche experimentation, existing regimes can also undergo transformation towards sustainability, being enabled by regime actors. Both experimentation and regime transformation are explored in five studies covering cities like Kolkata, New Delhi and Ahmedabad in India and Bangkok and Chiang Mai in Thailand. However, the majority of the thesis has a strong focus on Kolkata. Following an introduction, the thesis begins with a study exploring diversity in the meaning of sustainability of experiments in different social, spatial and systemic contexts. Focussing on niche experiments, the second study is an analysis of niche actors’ strategies to ‘empower’ sustainable innovations, negotiating with incumbent regime actors in legal and policy spaces. Looking beyond experimentation, a third study focuses on different transition pathways in megacity Kolkata’s public transport regimes. It proposes a new ‘mapping tool’ to identify changes in regime rules, trajectories and selection pressures. In the penultimate …