From the Yamato, Kamakura, Muromachi and Warring States periods through the Edo period, the Mutsu region underwent turbulent political, economic and cultural changes.
　In the Heian period, the imperial court defeated the Emishi (natives of Japan’s northern regions) and ruled over Japan. Imperial rule continued until the establishment of the Kamakura shogunate, when the warrior class seized power. Afterwards, Japan was ruled by the warrior class. 　During the Muromachi period, feudal warlords constantly fought each other for land and power. While being fraught with wars and disorder, the country fell into a chaotic period of warring states.
　Around that time, Mutsu Province (present-day Yamagata Prefecture) was ruled by the Osaki clan. To strengthen border security, the Osaki clan established a barrier station at Shitomae in the Naruko area, located on the border with Uzen (present-day Yamagata Prefecture) and Ugo (present-day Akita Prefecture).

　Myosada, Ogurogasaki and Mizu-no-kojima, which appear in Matsuo Basho’s The Narrow Road to the Deep North, have been well known since the Heian period as places of scenic beauty and have been described in many Japanese poems. Around 1689, when Matsuo Basho crossed the Shitomae-no-Seki barrier, the route passing through the barrier to Uzen (present-day Yamagata Prefecture) was extremely hard due to geographical features with high mountains and deep valleys.
　Today, by walking along the Oku-no-Hosomichi Dewa-Sendai Highway, tourists can follow the path that Basho took a long time ago, while enjoying the atmosphere of those days.