Hojo Ujiteru was one of the powerful lords of the Hojo family. He built this castle to strengthen the Hojo position in the area and help defend Odawara Castle from attack as well. After Odawara Castle was surrounded by Hideyoshi forces, Hojo Ujiteru, Ujimasa and Ujinao left to fight in Odawara leaving Hachioji-jo nearly defenseless. Soon after, Hachioji-jo came under attack from Hideyoshi forces On June 23, 1590 and fell in one day. Hideyoshi later went on to defeat the Hojo at Odawara and complete the unification of Japan. It is said that Hideyoshi feared Ujiteru for his intelligence and prowess and that is a large part of why he demanded Ujiteru to commit suicide ( seppuku after he was captured.

Hachioji-jo was a great sprawling castle across the mountaintop with barricades built in strategic places to stall would be attackers or spies. The picture above of the entrance to what was originally the lord's palace. It is at the base of the mountain while the castle was actually at the top. There are a few small pieces of stone walls around the top of the mountrain but that is all that remains. The palace stood at the top of the hill across the bridge and was heavily fortified.