The town had a tidal harbour on the River Brede. It flourished until the middle of the 14th century. It then suffered French and Spanish raids during the Hundred Years' War until the 15th century and was hit by the Black Death. In 1350, the Battle of Les Espagnols sur Mer was fought nearby. In 1360 the town was sacked and burnt by a French expeditionary force, sent in an unsuccessful attempt to retrieve their King John II of France captured at the Battle of Poitiers four years earlier. The town remained prosperous, although reduced in size until the 1520s. The silting of the harbour ultimately destroyed its prosperity. Camber Castle was built by Henry VIII in the early 16th century halfway between Winchelsea and Rye to guard the approach to the Camber. Much of the stone used in its construction may have been taken from the demolition of the Franciscan monastery of Greyfriars.