The purpose of this study is to create a streetscape simulation system to support local cultural succession by conveying—in a clear and simple way—local history and culture to interested members of the public. We developed an interactive system, based on a game engine, for the streetscape of Fujisawa-juku, which is a post-station town on the former Tokaido Road of the late Edo period. We designed 3D models for former architecture and urban facilities, using Ukiyo-e and old documents provided by the Fujisawa city archive as references. In addition, regarding dynamic spatial elemental components that encourage users to visually survey the area, we prepared non-player characters that walk in a specified range and communicate a fixed set of remarks. Furthermore, we created soundscapes, which correspond to particular locations, using sound effects in the 3D models by incorporating natural sounds. The developed streetscape simulation system is on permanent exhibition at the Fujisawa-juku Intersection Hall and is widely accessible to the public.