The status of urbanized areas has recently deteriorated as the need for people and goods transportation has grown. Bag Bazar Street is one of Kolkata's three main thoroughfares and is known as the grandmother road in the ekanto poribar (joint family), making it an ideal case study location. This paper aims to investigate the complete connectedness of Bag Bazar Street using urban morphology and space syntactic analysis. Syntactic space studies help investigate diverse historical sources to produce a cohesive account of urban spatial configuration by developing and evaluating hypotheses about urban mobility features and linkages across history. The research analyzes urban space and space syntax, which offers compelling opportunities as an exuberant proliferation of spaces. The city plan is critical in examining the historical link between metropolitan and urban life. When determining an area's level of connectivity, the aspect of spatial integrity must be taken into account. An axial map with a connection map frames essential findings in the study. Any plan for urban revitalization or smart city development requires a thorough understanding of the spatial characteristics and phases that define modern cities and the relationship between the two. Consequently, this study aims to confirm the degree of connectivity of Kolkata's Bag Bazar street as an input for future Smart city development. © 2022 IEEE.