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 portions to ascertain how much work was required, and in this he was to be assisted by the bailiffs.
In 1799, after he had taken down the gateway, the roof and most of the side walls, Foster found that his price of £31.2.10d was too low and asked for £48.
Charles Morgan, who was anxious to widen the Westgate Square, then came to the assistance of the town and offered to build a proper and sufficient prison at the east end of a dwelling house occupied by George Marshall, in Mill Street, in exchange for the old prison, together with the ground on which it stood, and the sum of £40.
His offer was accepted and the prison in Mill Street was soon built, for in 1803, an account was passed for payment for whitewashing the prison walls.
There is no doubt prisoners from Newport were sent to the old House of Correction at Usk. This building was converted from the old Bridewell in 1820 and as far as can be ascertained was in the vicinity of Usk Bridge.
This House of Correction was closed in 1843. The building known later as Usk Prison was built by the magistrates in 1843 as a new house of correction. The building was taken over by the Prison Commissioners on Ist April, 1878, under powers conferred on them by the Prisons Act, 1877, and was closed on 15th March, 1922. Prisoners have been sent since this date to Cardiff Prison.
The prison built in Mill Street, Newport, soon became unsatisfactory, and in 1837 a committee was formed to consider improving it, since it was considered unsuitable for the detention of debtors.
On 5th March, 1840, the Watch Committee took over the prison. They had a padlock fitted to the door and converted it into a police station, but two years later they closed it on the opening of the Town Hall police station.
Ten years later it was offered for sale and subsequently sold to the Great Western Railway Company on 8th August, 1873. No doubt, although called a prison, the premises merely comprised detention cells.
On 31st July, 1884, while Samuel Dean was surveying the demolition of the old Westgate Hotel, prior to erecting the building he was to occupy, workmen came across an old spiral stairway and at the bottom a stone porch, forming the entrance to a subterraneous passage or subway, leading under the road (Stow Hill) in the direction of the Ne Plus Ultra Inn.
Unfortunately, however, further investigations were not carried out and the passage was filled in. There still exists today, however, a passage about 7 feet wide and 7 feet 3 inches high under the site of the Ne Plus Ultra Inn. It extends for about 45 feet, and ends directly under the pavement building line.