This study assessed the effects of the constructivist approach on the development of historical thinking skill among Senior High School students and recommended a contextualized learning guide and rubric that targets historical thinking skill using a constructivist pedagogical approach. The study specifically determined the level of historical thinking skill among Grade 11 Social Science students of the Senior High School Department in a selected private university before and after the implementation of the constructivist approach in the teaching and learning process and if there is a significant difference between the level of historical thinking skills before and after the pedagogical intervention. This study also looked into the benefits and drawbacks of the constructivist approach as a teaching pedagogy towards the development of historical thinking. Constructivism has benefits and drawbacks at different stages of the learning process. As this is a different method than the more conventional pedagogical styles, consistent practice in the practical teaching strategies that encourage Constructivist learning is important in order to maximize its benefits and convert its constraints into potential. As an outcome of this study, the researcher created a Contextualized Learning Guide that took into account all of the findings from direct observations and focus group discussions.