The realization that our archaeological field school at the University of Toronto Mississauga (UTM) has operated, in its current form, for the last 12 years and has involved 200 students, and more impressively that the Boyd Archaeological Field School, run for 50 years, has provided 1500 students an opportunity to experience archaeology, has given us an occasion to reflect on field schools as an entry point into heritage careers. Focused largely on UTM’s Schreiber Wood Project Field School, we explore how the structure of our course, and related student experiential learning initiatives, aims to provide students with skills that are directly transferable to diverse careers in heritage. Here we bring together perspectives from the course instructor, staff, and two former course students who have gone on to careers in the heritage industry. We also touch on some ways in which recent, unexpected connections have developed between the UTM Field School and the Boyd Field School.