In recent decades, history and education scholars in the Western world have argued for a constructivist approach to disciplinary thinking in the teaching and learning of History, known as "historical thinking". Yet, there has been little classroom-based empirical research exploring how teachers engage with historical thinking theory, enact related practices in the classroom, and, in Canada, utilize historical thinking concepts. The multiple-case study outlined here addresses this gap, by offering descriptive details and insights regarding four Canadian secondary school teachers' attitudes, understandings, implementation, and applications of historical thinking in lessons and assessments. Differences among these teachers' perceptions and practices indicate that historical thinking is not a singular pedagogical approach. Yet, common elements revealed two broadly drawn typologies that may serve as inspiration and provide concrete examples for history teachers wishing to develop their own historical thinking practices. Rich descriptions also provide unique insights into how the teachers use their judgment and knowledge in the choices and decisions they make to move theory to practice. Finally, this study offers a methodology for the continued classroom-based study of historical thinking.