This article explores the aims and delivery of a living history event conducted in a contemporary urban environment. It reports on a pilot program, “Occupied Philadelphia,” delivered in October 2017 by the Museum of the American Revolution in downtown Philadelphia. This program re-created events and incidents from the fall of 1777 and included a walking tour with three main stops highlighting the lives of everyday Philadelphians and British soldiers. Occupied Philadelphia provided a framework for volunteer interpreters to engage in a form of “guerilla interpretation,” taking public history into unexpected places as a means of inspiring historical empathy and encouraging the public to make connections between the past and present.

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