The present research seeks to outline a common ground between the notions of urban aesthetics and inclusive planning by taking Siliguri Town station and its adjacent market as the cases. This article attempts to redirect the study of urban geography of Siliguri city away from macro-level analysis of space, which sometimes generates crude generalized discussions about the spatial development of urban landscapes, on the side of a more vigorous contemplation and critical consideration on the scope of micro-level planning alternatives for the city. Toward this objective, the research methodology is grounded on the analysis of historical databases, intensive field observation, and qualitative interviews. Through ten in-depth semi-structured interviews with key stakeholders including local body representatives, railway officials, planners, investors, as well as civil society organizations in Siliguri City, this study seeks to emphasize the factors that stakeholders in the city consider to be essential for the micro-scale development of Siliguri Town station neighborhood and its long-term effects on a number of actors. Findings from the interviews indicate that Siliguri Town station and its neighboring markets, such as Mahabirsthan and Hawkers’ Corner, are continuously growing as the places of urban contestation and struggle. To critically address these contestations, the research argues for the resurgence of Siliguri Town station neighborhood as the key urban territorial form for collaboration among central, state, and local government authorities as well as private players. The principal outcomes of this research, therefore, are expected to provide some micro-level planning alternatives, which can pave the path for an inclusive and planned production of urban space around Siliguri Town railway station, representing the heart of Siliguri city.