Creating an engaging lesson can be a challenge for secondary grade History teachers especially today with the added pressure of high stakes testing. In an age when History lessons have devolved into an endless multiple choice list of dates, places and names, history instruction has strayed further away from what it should be: an understanding of what life was like when. As teachers struggle to keep their students'' attention while covering what they must know, the study of history has lost its most fundamental benefit for the student, which is the opportunity to interpret and think critically. Presented here are two interpretation scaffolds, three lesson plans, as well as research which will aid teachers in their quest to develop the critical thinking skills of their students. The presented lesson plans use artworks as a window into the past and utilize the emotional connection people make with art as a strategy to engage students and bring inquiry back to the study of the past.