The original town of Winchelsea grew up as a Saxon fishing settlement during the 11th century. It was built on a massive shingle bank that extended northeast from Fairlight Head, across what is now Rye Bay, to Lydd and beyond. This location is at the root of Winchelsea’s name. The suffix -chelsea comes from the Saxon word chesil, which refers to a shingle beach or embankment. The prefix Win- may be derived from the word gwent meaning a level and refers to the marshland behind the old town. The historian Cooper reported the unlikely proposition that the prefix was derived from the word wind and referred to Old Winchelsea’s exposed position on the coast. Other authors have favoured wincel- meaning corner (of the great shingle bank) and win- derived from market.
Behind the great shingle bank on which Old Winchelsea was sited, a wide shallow bay called the Camber (from chamber) was formed by the conjoint estuaries of the Rivers Brede, Rother and Tillingham. The Camber provided a large tidal anchorage sheltered from the sea. Various tidal creeks emptied into it and ships would have anchored stem-to-stern along the channels and creeks, lying in the mud at low tide, as at Rye today. Old Winchelsea was probably sited on the tip of a promontory that commanded the break in the shingle bank that provided access between the Camber and the sea. On a hill on the northern side of the Camber stood Rye, and to the north and east, protected by the shingle bank, was the Walland Marsh, part of Romney Marsh.
The first documentary evidence for the existence of Old Winchelsea may be in the Domesday Book (1086), which recorded that the vast Manor of Rameslie, which extended from Hastings to Rye, included a novus burgus or new town with 64 burgesses. Some historians believe that this new town was Old Winchelsea. The Pipe Rolls (royal accounts) of 1131 and 1164-65 mention both Winchelsea and Rye, showing that these had become significant ports by those dates. The earliest surviving royal charter to the two towns dates from 1191, but this confirms liberties given earlier by Henry II (1154-89).
