In the following paper, a description, a comparison, a series of reflections, and future directions of two successful Contextualized Digital Heritage Workshops (CDHW) will be presented. The workshops have been organized during the eCAADe and CAADRIA conferences. The importance of architectural heritage as an expression of a local history and identity in a world that is more and more globalised is evident. Multidisciplinary and interdisciplinary approaches, together with the use of digital technologies open new opportunities in the comprehension, documentation, analysis, reuse and dissemination of architectural heritage. The main concept behind a CDHW is to connect the event (and its wide variety of participants) to a specific local context in a multidisciplinary way. The paper defines and proposes a methodology to critically evaluate the two workshops and their individual aspects in order to identify and investigate ideas that can be explored during future CDHWs.