Effective stormwater management of a community requires a comprehensive understanding of the watershed where it is located. Many studies have implemented the watershed approach to stormwater management. However, when reviewing the literature, a glaring disparity can be observed between urban communities and smaller underserved communities. Most work on watershed planning have focused on large urban areas, while very little effort has been put forth to understand and address stormwater issues in smaller underserved watersheds. Considering this disparity, our study initiated the development of a watershed-wide stormwater management plan for the town of Gainesboro, a small, underserved community in Jackson County, Tennessee. The town experienced significant flooding in June 2018 from water logging as well as Doe Creek, the nearby stream overflowing, that impacted the town’s Emergency Management Services building, the Jackson County Public Library, and surrounding residential and commercial areas. However, prior to this study, limited data were available to determine the factors contributing to the flooding. Through a Community-University Partnership Program (CUPP), relevant hydrological, sociodemographic, meteorological, land-use, soil and topographical data were collected. Historic flow data of the Doe Creek and its tributaries, flood maps, and sewer maps were also obtained. Preliminary assessment indicated the town’s poor stormwater management infrastructure as a plausible reason for the flooding. To address this stormwater pipes were also surveyed. All geospatial data are organized in a geodatabase. Its analysis in the future will allow for an informed understanding of the stormwater issues in Gainesboro, with the aim of developing effective mitigation measures.