This chapter deals with the early urbanization in the Bengal basin, which is the world’s largest deltaic system formed by the Ganga–Brahmaputra River system. Early urban settlements are found in three distinct regions—the Barind plains, the Hooghly-Bhagirathi basin, and the Deltaic region of Bengal. The urbanization process here, as deduced from classical literature, was definitely triggered by the Mauryan economic system due to contact with the middle Ganga plains and cannot be attributed to internal developments. The chapter highlights historic sites from the third century BCE with illustrations of material culture and cultural reconstructions. There is also evidence of contact with Indian Ocean trade in the early historic period, which finds ample mention in the classical texts, especially mention being made of ancient Tamralipta, which is historically directly connected with the present-day Tamluk in Medinipur. The chapter indicates the Bengal Delta urbanization as derivative and also occurring only in the early historic period, later than the ones that occurred in the western and central regions of the sub-continent.