During the early twentieth century, amid growing interest in the pedagogical significance of heritage landscapes, Pennsylvanians took a leading role in demonstrating the value of teaching with historic places. A forward-looking Pennsylvania Historical Commission (the Pennsylvania Historical and Museum Commission since 1945) and significant investments by the federally sponsored Works Progress Administration paved the way. This essay reflects on that history toward assessing the role of historic places in education today. It suggests that historic places offer important lessons beyond what they reveal about how Americans lived in the past. Most significantly, we gain new insight into Pennsylvania history by interrogating the reasons why historic sites are preserved and how their management changes over time. Several examples illustrate how challenging students with nuanced considerations of historic places encourages all of us to be mindful of persistent threats to Pennsylvania’s public historical resources.