The Westgate is one of two surviving gateways of the original five that stood along Winchester's city walls, the line of which was first drawn by the Romans, around 70 AD.
The present structure is medieval, although it stands on the site of the earlier Roman west gate. The scar where the city wall joined can be traced on the north side of the monument.
Until 1959, traffic entered and left the city through the main passage. The pedestrian way to the north was inserted in 1791, destroying thus a two-storied porter's lodge. The porter collected tolls and all goods entering the city and ensured that the gate was closed each night at the curfew bell.
Between the 16th and 18th centuries the upper chamber of the gate was used as a debtors' prison; the walls still bear the prisoners' graffiti. It was later used as a smoking room, which was demolished in 1940. In the 19th century the upper chamber housed the city's archives and in 1898, after extensive renovation, it was opened as a museum. Currently it displays Westgate's story, in particular highlighting Winchester's Tudor and Stuart history.
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