Climate change poses some of the most significant risks for the preservation of coastal cultural resources or cultural heritage. As a result, more research is needed to facilitate the design and implementation of feasible and transparent adaptation strategies for cultural resources under changing climate conditions. In this paper, we begin to explore the challenges and opportunities that face cultural resource managers as they begin to grapple with climate change adaptation planning in dynamic coastal environments. Specifically, we provide an overview of a value-focused, decision-analytic approach that was applied in a pilot test of climate adaptation planning for buildings within designated historic districts on the barrier islands of Cape Lookout National Seashore, North Carolina. We provide descriptions of the challenges that are uniquely facing cultural resource managers and initial evidence of the utility of this type of approach for informing judgments by presenting pre- and post-workshop survey data. Although additional research is critical to offer planning and policy guidance, we found that structured deliberations about cultural resource adaptation planning not only influenced participants’ opinions but also provided a necessary space to better understand the complexities of climate and budget uncertainties. Our evaluation is a first step at documenting the difficult and value-laden decisions that must be addressed by cultural resource managers as fiscal constraints and impending climate impacts threaten the traditional approach of preservation in perpetuity.