To the left of the Look Out, you will see the Strand Gate. It is worth examining it from the other side.
The Strand Gate is so called because it was built to defend the road that led up from the Strand, which was the harbourside area of the medieval port that ran along what is now Tanyard Lane (A259). The Gate is now thought to have been completed in about 1300. It was at least a third higher than it is today and incorporated two portcullises and a pair of gates. It would have been rendered and whitewashed. There was a porter’s lodge inside the front left-hand tower and a room for the portcullis winding gear on the first floor. The Strand Gate incorporated decorative stonework, some of which is still visible, suggesting that it has always been the main entrance into Winchelsea.
Strand Hill provided the background for the painting of The Blind Girl (1856) by Sir John Millais, the Pre-Raphaelite artist, who spent much time in Winchelsea.