Tolstoy’ encounter with the Japanese novel The Cuckoo (Hototogisu) coincided with the final period of his intellectual shift, a time when world history in the 1890s converged on the Siberia of Russia, Japan, and China, interacting with European revolutions, industrial capitalism, and scientific discoveries. The circulation of The Cuckoo in China, Japan and Russia reveals how intellectuals of different generations from these three countries engaged in the dialogue of ideas through literary texts within the historical context driven by Northeast Asian regional dynamics. Tolstoy’s constant reviewing of Chinese classics, his intense pursuit of modern Chinese texts in the last five years of his life, and his interactions with the younger generation of Meiji-era Japanese figures such as Konishi Masutaro, Tokutomi Sohō, and Tokutomi Roka, collectively forged the intellectual foundation his “turn to the East”. In this process, the encounters between literary texts, historical events, and figures triggered the emergence of Tolstoy’s world proposition. The metaphysical concepts and all the actions encompassed by “world” rapidly correspond to a vast historical context and spiritual spirit. By tracing back to the emergence of this world proposition driven by literature and region, and delving into the complex research literature and historical materials of Tolstoy, we can provide rich modern resources for expounding the idea of mutual learning among civilizations in the present era, restarting the research on regional literature and regional history, and responding to the world civilization form that is of common concern to humanity.