This article presents two case studies, from Scotland and the Scottish Islands, of communities' engagement with archives and their attitudes toward heritage. The case studies arise out of knowledge transfer between an historian employed in an academic role at a Scottish university and two “third sector“ organizations. By comparing the perspectives of historians, archivists, and community organizations the article shows the different ways in which these separate interest groups perceive the value of archives. It then points to some of the possibilities and challenges of working collaboratively to deepen understanding about the past and to create wider opportunities, now and in the future, for historical interpretation, teaching, learning, and research. In the era of digital technologies, it is recommended that undergraduate students be taught the key concepts of archival theory and practice, while also being encouraged to experience working with original archival documents.