The town suffered seven major attacks by the French in the 14th and 15th centuries and, in nearly every case the attackers entered the town where they burnt, slew and pillaged before withdrawing.
The Napoleonic Wars
Though Winchelsea and its fellow Cinque Ports eventually stopped providing the king’s navy, they remained on the ‘invasion front’. In the Napoleonic Wars the threat of invasion was very real. The flat coast between Fairlight and Hythe was the most vulnerable area and the Royal Military Canal was built as part of the defences against invaders.
It runs close below the seaward cliff of Winchelsea. Soldiers were stationed here, and the Mayor organised the call up of all men of the town suitable for service in the militia. The names of Barrack Square and The Armoury are reminders of these times.
During the Great War of 1914 -1918 there was no immediate threat of invasion, but troops were constantly passing through Winchelsea. Many were on their way to Folkestone or Dover and on to France. They were billeted with families in Winchelsea and some were employed in digging trenches for the defence of the town. Traces can still be seen in the field below Strand Hill. No enemy damage was recorded in Winchelsea. The nearest incidents were when a Zeppelin dropped a bomb near Pett, and when a British aircraft made a forced landing near Camber Castle.
The Second World War brought the threat of invasion again from the air as well as from the sea, and large areas of Pett Level in front of Winchelsea were flooded. At the start of the war Winchelsea was a reception area for evacuees, and within days of the declaration of war children from London arrived. A hospital for any who needed it was set up in White Close overlooking the church and manned by volunteers.
The New Hall became a school where the teachers who came from London with the children continued their education. But when the first bomb fell in the Marsh the children and their teachers were removed as quickly as they came, to safer regions. Winchelsea became part of a prohibited area which no one from outside could enter without a permit.
Troops were stationed in the town again, amongst them the 1st Battalion of the Royal Regiment of Canada which trained here in 1941 before taking part in a disastrous raid on Dieppe. At another time General (later Field Marshal) Montgomery and his staff occupied Greyfriars.
Bombs fell in and around Winchelsea, and a resident was killed when one fell at the crossing of Mill Road and Castle Street. Another was killed when a German aircraft returning home after a raid, discharged its remaining ammunition haphazardly over the town.