There has been a Mayor of Winchelsea since Edward I granted the town the right to its own Mayor and Corporation around 1292. Records of the Mayors exist since 1295. Since the Mayor has been elected annually on Easter Monday by the Freemen of the Town at an "Hundred".
The corporation lost its remaining civil and judicial powers in 1886 but was preserved as a charity by an Act of Parliament in order to maintain the membership of the Cinque Port Confederation. The mayor and corporation in Winchelsea now have a largely ceremonial role, together with responsibility for the ongoing care and maintenance of the main listed ancient monuments in the town and the Winchelsea museum.
The following is a list of persons who have held the office of Mayor of Winchelsea: