Envisioning Dalit emancipation, for Ambedkar, the acquisition of formal modern education and entry into urban spaces were two critical modern pathways for the liberation and economic empowerment of the community. Attaining education is a strategic liberatory instrument to dissociate from the defiling ascriptive work be able to access modern and respectable occupations. He held that Indian villages, organised around the orthodox social structure of the caste system, are anti-democratic dystopian spaces that deny dignity and equality to Dalits, staying away in ghettos isolated from the villages. To understand the possible emancipatory potential of the metropolitan city, the chapter examines whether ‘the city is truly bereft of caste identities,’ as Ambedkar imagined. Does it offer avenues and ‘choices’ of socio-economic mobility to all regardless of caste identity?