The concept of site-size hierarchies has traditionally been used by archaeologists to ascertain the complexity of political entities within their territories on the basis of regional settlement survey. However, a unilineal and uniform assessment of site sizes as the basis for addressing ancient South Asian cultural development and political complexity is both inadequate and misleading. Landscape disruptions (farming, dams, modern settlements) often obscure ancient site sizes, and in any case sites can be “important” well out of proportion to their areal extent. Religious sites are particularly dynamic because they expand and contract during periods of pilgrimage and according to the seasons. Our long-term research project focusing on the Iron Age and Early Historic periods in coastal Odisha has investigated sites at a variety of sizes, ranging from villages to the intensively-occupied and long-lived ancient city of Sisupalgarh. In addition to these habitation settlements, there are numerous distinctive Buddhist and Jain sites located at a distance from major population centers, including Khandagiri/Udayagiri, Dhauli, and Aragadh. Located in elevated and conspicuous places, these religious sites were active parts of the “quotidian activities” of settlement-dwellers in ways that were more impactful than size alone would convey. Given the social and economic relationships among sites of different types, we examine the way in which areal dimensions are only one measure of regional cultural and sociopolitical integration.