Postcard from a set of 'Ancient gates of Canterbury', and drawing.
The houses to the right still survive... note how different they look in each illustration.

Wincheap Gate was not properly speaking one of the medieval City gates. It came into existence perhaps in the 16th century when the highway through the Castle Yard was blocked up, and a diversion was made round what is now Worthgate Place and through a gap in the City Walls, which was formed into a Gate though without any elaborate defences.

The name of the gate is taken from the nearby Wincheap Street, a subject of much disagreement as to derivation. Perhaps it means Wine Market; at any rate the name was in use by A.D. 1200.

By 1582 the gate was sufficiently old to require repairs, when a turnstile was fitted into it. In 1670 William Jacob, the local doctor, rebuilt it, and was rewarded with a dinner at the expense of the Corporation.

The gate now consisted of two brick pillars, surmounted by stone balls, with a simple arch. The pillars were based on a plinth of stone apparently of Norman workmanship, undoubtedly plundered from the ruins of some decayed religious house such as St. Augustine's Abbey. Above the arch on the outside was the inscription Welcome and on the inside Farewell. The gate was partly pulled down in 1770, but one of the brick pillars still survives. [Does it? I'll have to check..!]