Adaptation is a central issue in climate change research and crucial questions on the subject include the challenges that affect its operationalization at the local scale. However, information on how to examine these challenges and determine their characteristics is limited. Using a modified version of Ostrom’s Institutional Analysis and Development framework, this paper addresses this gap through a case study in Albay, Philippines, with special interest on the challenges in mainstreaming climate change adaptation (CCA) into local land use plans. The paper developed 20 quantitative indicators to examine the nature of and linkages among these challenges. The mainstreaming indicators were computed using data gathered from a survey that incorporated a scorecard to quantify the respondents’ answers; the survey was conducted among the key players in local land use planning in Albay. Correlation analysis showed that there are strong linkages between the challenges associated with local leadership, local government prioritization, and local government’s commitment to CCA. Analysis of the mainstreaming indicator scores suggests that the challenges can obstruct mainstreaming of CCA at varying degrees of severity; when overcome, they become significant opportunities for the effective operationalization of the approach. The paper offers analytical tools that have the potential to help planners make informed decisions concerning the challenges in mainstreaming CCA, and formulate practical strategies for its implementation.