Before Doppo Kunikida consciously described the anonymous landscape in “Musashino” and “Wasureenu hitobito” in 1898, he had spent approximately 10 months as a teacher in Saiki, Oita, from 1893 to 1894. This study aimed to clarify Doppo Kunikida’s interests and perspectives, focusing on the events in Saiki. First, a quantitative text analysis of the diary “Azamukazaru no ki” revealed that Doppo Kunikida was pursuing the relationship between “humans” and “nature,” and that he was interested in the situation of “humans” living in nature and towns, recognizing it as “facts.” Next, the relationship between human, landscape, and emotional descriptions in the five literary works showed Doppo Kunikida’s following perspectives: 1) the contrast between the lively people and the desolate town, 2) the contrast between the traditional life and the town’s changes, and 3) the nostalgia felt when he left the town and placed himself in nature. Thus, Doppo Kunikida’s awareness of the anonymous landscape was caused by 1) auditory perception, 2) a sense of time, and 3) his physical perspectives. The meaning of the events in Saiki, leading to “Musashino” and “Wasureenu hitobito,” was that he repeatedly felt “the landscape” vividly and realistically, using the above perceptions.