These fortifications were rendered necessary by the _inning_ of the shallows which separated Rye from the mainland, the sea having set to work, with the true ironic touch, depositing shingle where salt water was essential, and irrupting where it was most unwelcome. And, sure enough, as the one enemy did its worst, filling in the harbour and making access to the little hill more easy, so the other enemy took advantage of the facilities offered, and the raids of the French gradually became more frequent and more severe. In the fourteenth century things were parlous for the island town. When it was not the turn of Winchelsea, Rye suffered, and vice versa. They set upon the town in 1337 with no great success, but in 1360 they spoiled both Hastings and Rye. Immediately after the death of Edward they came again, and "within five hours brought it wholly into ashes, with the church that was there of a wonderful beauty, conveying away four of the richest of the towne and slaying sixty-six; left not above eight in the towne. Forty-two hogsheads of wine they carried thence to the ships with the rest of their booty, and left the towne desolate."
In 1378 the men of the Cinque Ports took some sort of revenge, according to the following interesting account in Fuller's _Worthies of England_: "May never French land on this shore, to the losse of the English! But if so sad an accident should happen, send them our Sussexians no worse success than their ancestors of Rye and Winchelsey had, 1378, in the reign of Richard the Second, when they embarked for Normandy: for in the night they entered a town called Peter's Port, took all such prisoners who were able to pay ransome, and safely returned home without losse, and with much rich spoil; and amongst the rest they took out of the steeple the bells, and brought them into England, bells which the French had taken formerly from these towns, and which did afterwards ring the more merrily, restored to their proper place, with addition of much wealth to pay for the cost of their recovery." But their triumph was short-lived, for in 1380 the place was again burned, despite the wall. Comparative quiet then reigned till 1448, when the last and most terrible invasion occurred. Then, according to Jeake, Rye was entirely burned, with the exception of the Landgate, the walls of the parish church, Ypres Tower, and the so-called Chapel of the Carmelite Friars in Watchbell Street. The town was devastated to such an extent that it was unable to furnish its quota of ships to the navy.