In the middle of the 14th century the Westgate tollbooth, with its residence for the bailiff over the arch and prison underground for delinquents, stood at the foot of Stow Hill, at the top of Skinner Street and adjacent to the Town Pill, where the river Usk washed the shores of present-day High Street. The tollbooth remained a place of confinement for prisoners from 1348 until its demolition in 1799. It was built in Gothic style in red gritstone, and bore the arms of Ralph Stafford, who was lord of Newport, a shield charged with a chevron on each facade.
There is reference to this prison in the report of a parish meeting held on 14th February, 1798, at the dwelling house at the Old Sloop, to consider the need for repairs to the prison. Notice had previously been published in church, it was resolved and agreed by the inhabitants present that there was need for repairing certain parts of the gateway or entrance and that any rubble or material left over should be sold to the best bidder. One, William Foster, who was present at the meeting, was requested to prepare an estimate after he had taken down certain … Read the rest