This paper explores the relationship between the teaching of history (the academic study of the past) and the teaching of heritage (meaningful stories tying people to a collective past). The research was conducted in a Jewish high school whose explicit mission involves teaching history through a US history course and heritage through an Israeli history course. Yet in reality, both classes, in different ways and to different effects, were engaged in a shared quest to help students understand the past and find meaning in its stories. This paper shows that history and heritage--often viewed by scholars as distinct enterprises--are neither clearly delineated nor mutually exclusive within the context of high school history education. By exploring two different attempts to navigate the murky waters of history and heritage, this paper highlights the tensions that arise when teachers aim to help students find personal and collective meaning, as well as intellectual stimulation, in their studies of the past.