Digital storytelling is an engaging learning environment that gained worldwide popularity over the last years. It offers a rich cross-curricular learning environment within which children design, create and present their own stories and develop many skills including literacy, presentation and communication skills as well as inquiry-based learning and digital skills. In this paper we present a new way of digital storytelling, a form of dramatized storytelling inspired by the rich tradition of Shadow Theater. This form of storytelling showcases an engaging way of renovating cultural heritage with the use of digital technologies. It combines a number of digital tools for the production of the digital stories covering all five phases of film making: scenario development, pre-production, production, post-production and distribution. eShadow can be used (a) to create digital shadow puppets, and (b) to set up, perform and record the scenes of the digital story (production phase). This way, digital story creation is wrapped around engaging learning scenarios, playful improvisations and creative learning. eShadow has been extensively used to support cross-curricular learning mainly in Greek schools. It is extended to support marionette-like interactions to promote its use in countries with relevant storytelling cultures.