This was the recognised position for the look out man in the days of the French wars. From here you can see the whole of Romney Marsh.
In the middle is Dungeness, at whose centre is the town of Lydd. On the skyline are Dungeness Lighthouse and the Nuclear Power Station. On exceptionally clear days it is possible to see the tops of the downs at Boulogne while, on clear dark nights, just before rain, the French coastal lights show up from Cap Griz Nez to Etaples. This is probably one of the best views of Rye, over two miles away, crowned by St Mary’s Church.
When Winchelsea was new, the Lookout and all the walls nearby were crowded with folk including Queen Phillipa of England drawn to watch the great battle of the Spaniards at Sea, when the English fleet under Edward III met their foes off Dungeness and the fight drifted into Rye Bay. On the English side were the heroes of Crecy and Poitiers: Bohun, Lancaster, Salisbury, Warwick, Manny, Chandos, the Black Prince. For the numbers of enemy vessels captured, this “Sea Battle of Winchelsea” came near to rivaling Trafalgar itself.
Not far to the right of Rye Town stands Camber Castle, built by Henry VIII on what was then a spit of land jutting into the sea. It could control the harbour of Rye and the entrance to Camber, now a faint depression and a narrow creek behind Rye Golf Course, but then a wide channel that was the main anchorage for ships sheltering or preparing to enter into the narrower water of Rye port. The central tower of the castle was built about 1490 and the remainder about 1539. The castle was dismantled about 1650 and left to decay.
Further south again, among the houses of Winchelsea Beach is the remains of the 18th century “cut” and new port of Rye, which took sixty years to build and was open for less than two. The ends of the old stone jetties may still be seen in the shingle at Dogs Hill.
Almost at the foot of the hill is the Royal Military Canal. Constructed during the Napoleonic Wars it runs right round Romney Marsh from Fairlight to Hythe.