The aim of this explorative study was to develop and test a pedagogy aimed at promoting students’ ability to perform historical contextualization. Teaching historical contextualization was conceptualized in terms of four pedagogical design principles: (1) making students aware of the consequences of a present-oriented perspective when examining the past, (2) enhancing the reconstruction of a historical context, (3) enhancing the use of the historical context to explain historical phenomena and (4) enhancing historical empathy. The effectiveness of these principles was explored in a lesson unit focusing on the seventeenth and eighteenth centuries. In a quasi-experimental pre-test–post-test design with experimental and control conditions, the effects of the pedagogy on 15- and 16-year-old students’ ability to perform historical contextualization were examined (n = 131). The results indicated that students in the experimental condition significantly improved their ability to perform historical contextualization compared to students in the control condition. These findings could be used to help teachers and other educational professionals design and implement historical contextualization tasks and instructions.