During the last decade we have witnessed the rapid development of interactive documentary, today demonstrating a great variety of documentary works, exploiting new technologies and new paradigms in nonfiction storytelling. Being at the epicentre of major transformations, which are taking place within contemporary media landscapes, interactive documentary is constantly experimenting with the cutting-edge technologies and producing innovative projects often challenging existing documentary praxis. In this chapter I will first examine the distinct features of interactive documentary that separate this new emerging genre from conventional linear documentary film, and give examples of different types of documentary projects. I then focus specifically on discussing interactive documentary as a form of digital mediation of cultural heritage. Alongside analysing interactive documentary applications used in the field of cultural heritage and cultural tourism, I examine the experiments in digital documentary storytelling undergoing at the Television Directing Department of Saint Petersburg State Institute of Film and Television. I use Maria Rozhina’s student web-project Oma Randu to investigate the following issues: How should we apply the benefits of interactive documentary to make historical and cultural heritage of the region more attractive for the residents and a wide range of audiences? And, secondly, how should we present intangible digital heritage objects as part of a coherent narrative?