The present book is a story of three roads of Calcutta which at various historical stages had produced diverse political and socio-economic currents, and led to the growth of institutions that had shaped the minds of Calcutta?s citizens. To put it in terms of an extended family, the first road Bagbazar Street could be described as the granny, spreading her progeny of lanes and by-lanes. The second road, Theatre Road, played the extraneous role of a midwife bringing to birth a hybrid Indo-European life-style and architecture that bore the signature of the colonial era. The evolution of the next road, Rashbehari Avenue, looks like the growing up of a middle class Bengali housewife gingerly stepping out into the limelight of modern society. By narrating their history, the author analyzes the socio-cultural and politico-economic changes in the city since its birth, through a critical synthesis of micro and macro perspectives that combines views from both above (official archives) and below (popular perceptions). The narrative ends with a brief critical examination of the new stage today in the urbanization of Calcutta - the city?s expansion into a globalized megalopolis renamed as Kolkata - through its extension in the recently constructed New Town, where the road system is being designed in a way that curbs the mobility of the common pedestrians and shrinks the democratic space that they still enjoy in the old three roads.