This paper considers Natsume Sōseki’s spatial analysis of Kyoto in his first essay for the Asahi Newspaper, “Kyo ni tsukeru yu” (Arriving in Kyoto One Evening, 1907). His essay depicts one path through Kyoto in 1907, overlaid with a second route traveled earlier with Masaoka Shiki, now deceased. While seeming to engage in traditional travel writing modes, naming famous places and attaching a poem at the end to memorialize his visit and his loss, the essay finds uncanny rather than comforting the apparent permanence of the spaces of Kyoto, and is equally disturbed by the speed of his arrival from Tokyo by train. The paper considers his essay from the perspective of cartographical theories with particular attention to the relationship between image and text elements and the potential for depicting or eliciting affect through maps. How might we think about Sōseki’s attention to the relationship between poetry and pictures as explored in Kusamakura in terms of his mapping of Kyoto? How does he employ senses not usually included in cartography (the taste of a piece of citrus or the coldness of using a certain type of futon) to develop and problematize standard imaginings of the layout of the city? What is the essay’s sense of the relationship between history and the mapping of modern spaces? Finally, while Sōseki’s essay suggests potential for digital humanities mapping, it also produces its own methods for mapping that problematize digital cartographic practices.