You won’t find any souvenir shops or vending machines near Shiroyama, but the little tourist information booth will provide you with walking sticks and maps, and the friendly Japanese-speaking guides offer good advice and free tours of the area (9am-4:30pm).
Hachioji Castle was built in the 1570s by Hojo Ujiteru, but fell to the forces of Toyotomi Hideyoshi in just one day in 1590, in a battle so brutal that the Shiroyama River is said to have turned red with blood. Ujiteru was forced to commit seppuku, the castle was ordered destroyed, and for centuries the site remained abandoned, as it was believed to be haunted. There isn’t much left of the structure today, but a small portion was rebuilt in 1990.
Shiroyama offers picturesque views and an interesting historical setting, so put your hiking boots on and go explore the remains of the castle, along with the small shrines dotting the mountain. After descending, be sure to visit the site of the lord’s palace, where the bridge, walls and entrance have been reconstructed to give you a sense of its former grandeur.
Take the JR Chuo or Keio line from Shinjuku to Takao (¥540 or ¥350, respectively), then catch a No.1 bus to Reienmae (¥180, 10 minutes). Walk west for 20 minutes, following the signs.