Stories put us in touch with ourselves, others, and our surroundings. Using innovations in multimedia technology, student and adult audiences can make personal connections to visual art and museum artifacts through new ways of storytelling. Digital storytelling is a new medium for this age-old practice and one that is humanistic, culturally rich, and globally relevant. This paper will review the pedagogical dimensions of a digital storytelling tutorial for K-12 teachers that took place at the National Gallery of Art's Teacher Institute in the summer of 2003. It will also examine how the concepts presented have been translated into real-world experience in Chicago public schools. The value of digital storytelling - for teachers and for museums - will be addressed through the perspectives of the museum educator who organized the Institute, a language arts teacher who served as a technology coach, and a program enrollee who develops on-line educational resources for Chicago public schools.