In 1548 Worth Gate was blocked and a new street (Castle Row and Worthgate Place) was formed to by-pass the castle. This new road which went round the bailey wall and ditch on the east had a new opening, Wincheap Gate, created for it in the city walls. The new gate, together with an existing postern to the west of the castle, led out onto Wincheap Green (now covered by a roundabout) where there was a gallows which is clearly shown on a map of Canterbury of c. 1640.
Outside the gate two timber-framed buildings were constructed, both of which survive. The structure to the west may have been a gate keeper's lodging. That to the right was a public house until the early 1960s called the Man of Kent.
In 1670 Wincheap Gate was entirely rebuilt in brick and at considerable expense by an emminent city physician, Dr Jacob. This new gate, which re-used the jambs of the earlier gate, was an elaborate affair with stone dressings. finials and inscribed stones bearing the salutation 'Welcome' and 'Farewell' on either side of the gate opening.
By 1770 the gate was in a ruinous and dangerous state and the upper parts were taken down at the request of the inhabitants of St Mildred's parish. The surviving western jamb was taken down when Dane John House was extended in 1773. The eastern jamb with Caen stone blockwork of the first
Wincheap gate survives today with a stone marked 'Farewell' reset in this position in 1833.
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