In this paper, we originally examine to write another version of Ryotaro Shiba’s historical travel essays: Kaido wo Yuku, whose topics he did not deal with well. Our topics is specifically focused on Kanashima region in Shibukawa city, Gumma, Japan, which is located at the interface, or boundary between plains and mountains in the Kanto district. This region contains volcanos, as well as remains of ancient iron factories and horse pastures. We aim to illustrate the Kanashima region via a multi-layered historical landscape, employing the interdisciplinary Shiba’s KANSEIaffective philosophy. Our portrayal is characterized by his keen insight, which penetrated the deepest historical layer at the local sites. Thus, the present work is supported not by a rigidly philological approach, but by a hands-on and imaginative approach based upon the fi eld experience.