The Yusaka road was the main route through Hakone during the Kamakura period (1195-1333). The road was established in the 9th century and cuts through the central mountains of Hakone from Yumoto to Ashinoyu and then on to Lake Ashi. The trail is now one of the main hiking courses in Hakone taking you through various natural settings and past the former sites of castles.

Originally the main course for travelers through his part of Japan was past the base of Mt. Fuji through present day Yamakita town. However, after an eruption of Mt. Fuji in 802 made this route impossible to pass and the Yusaka road became the main route. The road is also known as the old Kamakura road. The Tokaido road would later become the main route for transportation after the Tokugawa Shogunate (1603-1868) committed to improving and reconstructing the roads of Japan when it came to power. Tokugawa Ieyasu (1543-1616) would establish his capital in Edo (modern daya Tokyo) and the traffic between the imperial capital of Kyoto and the political center of Edo increased significantly.

The trail was used by Minamoto Yoritomo (1147-1199), the founder of the Kamakura shogunate when visiting religious sites in the area such as Hakone Shrine and Mishima tiasha shrine. Along this trail are the former locations of satellite castles of Odawara castle during the Sengoku period of civil war in Japan (1467-1615).