Watersheds are natural-ecological regions characterized by a strong sense of unity. In contrast to the current administrative jurisdictions, watersheds form natural units guided by common hydrological, climatic, and, increasingly, cultural landscape planning mechanisms. The main purpose of this chapter is to shed light on a novel approach to using watersheds to inventory, preserve, and promote cultural landscape resources. The Hudson River region of New York (USA) is examined to assess the formation, evolution, and preservation of cultural landscape resources between New York City (south) and the state capital, Albany (north). It includes mixed methods, combining literature reviews on regional planning, professional practice, and multi-scalar governance with selected case study analysis and the assessment of policy priorities. The significance of this research is in the application of a novel cultural landscape resources planning approach to the study of the Hudson River region of New York.