The historic New York City (NYC) Watershed Memorandum of Agreement signed in 1997, which established the Watershed Protection and Partnership Program (WPPP), aimed to safeguard water quality for downstream NYC communities and enhance community vitality within the upstream watershed. Up to now, the focus has been on maintaining water quality, with less attention on the socioeconomic and demographic well-being of the upstream communities. This study bridges this gap by examining the socioeconomic and demographic trends within the upstream watershed communities. We collected census data from the U.S. Census Bureau and American Community Survey (ACS) from 1990, 2000, 2010, and 2020. The data were collected primarily for the Catskill-Delaware Watershed region, as well as the five immediate watershed counties, New York State, the U.S., and two rural counties similar in population density to the Watershed to serve as comparison areas. This study analyzed demographic factors and economic, and community characteristics to identify trends and shifts over time. Our findings reveal the demographic shift towards an older retiree population, decreasing labor force, higher unemployment rates, higher disparities in income distribution, and longer commute times in the Watershed compared to our comparison areas. The Watershed also experiences higher home vacancies than the comparison areas, suggesting a shift towards seasonal or second-home use of properties. While this study offers insights into socioeconomic and demographic shifts in watershed communities, its reliance on census data may limit the precision in establishing causal links between watershed protection measures and these shifts. Incorporating qualitative analysis in future research will deepen our understanding of these relationships.