Cooling Castle, a mile east of Cliffe, was built for Sir John de Cobham, a license to crenellate being granted in 1381. Two years before, French raiders had caused devastation on the Hoo peninsula, so Cooling was built at least partly with coastal defense in mind.
Ironically, but not uncommonly where English coastal fortifications are concerned, the castle saw no action against foreign invaders but became embroiled in civil strife. In 1554, Sir Thomas Wyatt sought the aid of Lord Cobham in the rebellion that he was organizing to prevent Queen Mary marrying Philip of Spain. When Lord Cobham refused, Wyatt marched upon Cooling Castle and breached its walls by cannon fire in the space of a few hours. After the episode, the castle was abandoned.
The castle is one of those later medieval castles which is split into two enclosures comprising a residential inner quadrangle and a much bigger base court, which housed the retainers’ lodgings and ancillary buildings. Its low-lying site would have appeared stronger when the moat was full of water.
The outer curtain and its rounded angle towers are now very ruinous, but the outer gatehouse is well preserved. This is actually just a gateway flanked by open-backed, half-round towers. It is curious that machicolated parapets crown the towers but not the gateway.
The inner courtyard is reached through another gatehouse flanked by rounded turrets. Keyhole gun ports appear here and elsewhere in the walls. To the right of the gatehouse, the curtain is embellished with alternate panels of stone and flint, creating a checkered effect. The corner tower here has vanished, but the round towers at the other three corners, along with much of the intervening curtain, still stand. These towers were machicolated as well. Within the courtyard, the only domestic feature to survive is a vaulted undercroft, which carried the solar.