Many school districts across North America have turned to a framework for curriculum design and instruction called "Understanding by Design." Included in the framework is a call for teachers to create "essential questions" that provocatively ask students to consider and learn the "big ideas and core processes within the content standards" (Tomlinson and McTighe 2006, 26). Essential questions guide teaching and engage students in uncovering the important ideas at the heart of a subject (Wiggins and McTighe 1998, 28). The conceptual foundation for this curricular approach and for this research is student-centered learning. Although essential questions are being widely used across content areas, a robust field of research specifically and concretely considering how exactly these questions are best employed does not exist, especially not for history courses. Through a mixed methods approach, this practical action research project determined that revisiting the same essential questions throughout the school year greatly increased students' abilities to connect learning between units, but only slightly increased their abilities to connect learning to personal experiences outside the history classroom.