The paper explores the processes, tropes and signposts of the Early Historical urbanisation and urbanism of India from the vantage point of the region of Odisha, which is generally ascribed to have witnessed social complexity, state society and urbanism in the Post-Mauryan Period in the second century BC on the model of the primary state of the Mauryas. Based on the archaeological evidence from different geo-eco niches of Odisha, the paper argues for the emergence of certain degree of cultural unity in the Early Historical period as marked by the entry of new elements in the material culture, such as fortified settlements, trade and exchange networks with other regions of the Indian sub-continent and the Bay of Bengal regions, writing, coin, water structure, kingship, Buddhism and Jainism. At the same time, the Early Historical settlements’ distribution, their origin and development and more importantly and their differentiation reveal their long evolution as well as their diverse nature and forms. Many of these complex habitational settlements revealed long period of evolution from the Chalcolithic and Iron Age, attracting more people to converge in the settlement centres at a later period. They were largely coherent settlement centres with their respective interaction sphere with other settlements. Hence, the paper questions the centrality of the Mauryan intervention as prime mover of societal formation in Early Historical Odisha and questions the way various geo-ecologies of Odisha have been seen as core and peripheral areas from the perspectives of the centre-periphery with the Gangetic valley as the metropolitan centre, Bhubaneswar and coastal Odisha as core and other geo-ecologies of Odisha as peripheries. Taking a longue duree perspective of the evolution of the settlements of the Early Historical Odisha, the paper argues for the growth of differentiated but networked settlements in Early Historical Odisha.