Bangladesh has historically relied on its rivers, canals, and water bodies for transportation and agriculture. In the southern regions, canals were crucial for socio-ecological life but have suffered degradation due to urbanization. This paper focuses on the Damodar Canal in Pirojpur, which has narrowed from 15–20 feet to 4–5 feet due to encroachment and waste disposal, resulting in a clogged urban drain. Despite these issues, it still supports local livelihoods and cultural practices. The study explicitly aims to restore the canal’s historic and functional significance through three targeted objectives: analyzing its spatial transformation, assessing the current environmental and socio-cultural conditions, and proposing strategic redevelopment initiatives. This research explores the potential to revitalize the canal through sustainable development strategies, including ecological restoration, establishing buffer zones, promoting water-based economic activities, and enhancing public connectivity. Conducted as part of a studio project in collaboration with the Urban and Regional Planning Department (UDD), the methodology encompasses field surveys, land-use analysis, spatial mapping, and a review of secondary data. The focus is placed on a critical 2 km stretch of the canal between the Baleshwar and Kocha rivers, chosen for its urban concentration. The findings reveal severe environmental and infrastructural challenges, including sewage discharge, stagnant water, and rampant, unregulated construction. At the same time, the research underscores the canal’s indispensable role in sustaining community identity, cultural heritage, and local livelihoods in Pirojpur. By positioning these findings alongside comparable restoration initiatives, the study makes clear that site-specific documentation is a vital foundation for developing integrated and sustainable rehabilitation strategies. The research illustrates that a thorough site analysis not only uncovers critical threats but also reveals significant opportunities that will guide future canal-front redevelopment and ecological restoration efforts in the Damodar Canal, Pirojpur.