In 1331, when Emperor Go-Daigo attempted to overthrow the Kamakura shogunate in the Genkō War, he relied on Prince Moriyoshi and a local lord from the Chihaya-Akasaka area, Kusunoki Masashige to raise an army.

However, this first attempt failed, and Emperor Go-Daigo was captured and exiled to the Oki Islands and Kusunoki Masashige faked his death at the Siege of Akasaka and escaped into the deep mountains of his own territory where he constructed Kami-Akasaka Castle and Chihaya Castle.

[4] The castle was consisted of several enclosures protected by dry moats, spread over the mountain and formed a letter "H" connecting two peaks and the intervening saddle.

In early 1333, Kusunoki Masashige joined forces with Prince Moriyoshi and recovered Shimo-Akasaka Castle and resumed his offense against the shogunate.

The castle fell after two weeks, once the shogunate army had managed to break the water supply to the defenders.