Flooding is a recurring event in the water cycle that has the potential to devastate what is in its path. Climate change is projected to make flooding worse in the Northeastern United States because of increased intensity of rainfall. An increase in the number of flooded homes where homeowners choose not to rebuild in place can be viewed as a symptom of climate change. These issues take place at the confluence of land and water, the balance of humans and our environment, and what can be learned from the past and from projections and models of the future. How can flooded sites that are not suitable for rebuilding be adaptively reused to leverage their ecological, social, and economic value? This question is assessed through a multi-scalar examination of a series of FEMA buyouts along the Kaaterskill Creek, a rural tributary to the Hudson River in New York.