The paper deals with the specific approach to teach the subject of assessment and retrofitting of historical timber structures to students of various colleges in an integrated and multidisciplinary course. Timber structures belong to the oldest structures in the world and because of their specific susceptibility to ageing, often require a profound analysis with respect to their current state and functionality. Especially in Europe, city centres are full of historical buildings that present an important cultural heritage, and as a consequence have a protected status. This status entails that these structures need to be assessed, maintained and monitored carefully, to keep the state of these structures at a level that they can perform. These tasks are often complicated and require interdisciplinary work. In education, this interdisciplinarity is often difficult to incorporate in the curriculum, as various expertises needed for cultural heritage assessment are separately and often fragmentary present at various colleges or faculties of universities, if present at all. Also, different teaching approaches may hinder course development. This paper deals with educational activities that have been developed and experienced at TU Munich and TU Delft, along with the cooperation with the University of Zagreb, dealing with the most important aspects of the assessment and analysis of historical timber structures.