Chepstow was the first castle that I ever visited, at the age of six, accompanied by my father, who was also seeing it for the first time. I was fascinated by the ruins. This was the beginning of an interest which has lasted throughout my life.

When seen from the English side of the Wye, this castle is a spectacular sight, stretching along the high limestone cliffs; and it would have been built in stages through the centuries, but most of the remains date from the thirteenth century

Established in 1068 by William FitzOsbern the cousin of William the Conqueror, just two years after the Battle of Hastings this  was the first stone castle to be built in Wales. It provided a suitable base from which his forces could push the conquest further west. By the time of his death in 1079 at the battle of Cassel in Flanders, he had subdued the main part of what later became the county of Monmouthshire. 

Initially, this castle  was known as Striguil, from the Welsh ystraigyl (signifying ‘Castle of the Crook’) which referred to a bend in the river Wye; apparently there are numerous ways of spelling this name. By the fourteenth century, it was simply known in English as Chepstow, from the Old English ‘cheap’ or ‘chepse stowe’ (market place) because in 1294 the town had been given permission for a weekly market 

Situated on the edge of a  90ft limestone cliff overlooking the Wye the ruins cover an area of 30 acres. On the land side it was defended by a deep ditch known as the Dingle, from which stone was excavated for building this remarkable castle, which has been described as the oldest post-Roman fortification in Britain.

I remember, as a child, looking up at the battlements and seeing figures standing there which did not appear to move and I commented to my father, “Those men are standing very still and they seem to be watching us!”. Later on, we climbed the winding stone steps leading up to the battlements and then realised that the five realistic figures representing defenders of the castle were just made of stone and have been keeping vigil there for 800 years.

The entrance to the castle is protected by two flanking towers and above it are the arches of the machicolations – openings through which boiling oil or heavy stones could be poured onto the heads of invading soldiers. This twin towered gatehouse which is said to be the finest example in Britain, was built in the 1190s by William Marshall (Earl of Pembroke) and the massive rectangular tower also bears his name. 

The old entrance gate with its sturdy  trellised oak planks held together with iron bolts  was hung (according to tree-ring dating)  in 1190, and still intact, it is claimed to be the oldest surviving castle gate anywhere in Europe. But  in 1963 it was removed to be displayed inside the castle as an important exhibit for it was never breached and undoubtedly impregnable.

Ancient gate
The ancient gate (Photo supplied)

The Great Hall begun in 1067, is the oldest part of the castle; it originally stood alone and it guarded the main river crossing from southern England into Wales. In due course Roger Bigod the 5th Earl of Norfolk  turned it into a magnificent banqueting hall, 90 feet long and 30 feet wide, and here in the days of Edward I, venison would no doubt have been served to the noble guests.  This great hall is about eight feet above the level of the court and steps lead up to its main entrance. Contained in the thickness of one wall is a narrow staircase which once gave access to an upper chamber or gallery, and then on to the ramparts.

On May 11th, 1648, Oliver Cromwell with his army arrived at Chepstow and they had no trouble in capturing  the town, but failed to take the castle, so he left his soldiers to reduce the Castle by siege, while he went on to deal with other troubles further west. 

This siege resulted in the Royalist defenders running short of food and the castle commander, Sir Nicholas Kemeys realising that he needed to plan a means of escape, arranged for a boat to be moored  in the Wye below the Water Gate, so that at the last moment, he and his men could make their escape across the river. Unfortunately the boat was spotted by one of the besieging soldiers, who bravely swam across the Wye with a knife between his teeth, cut the boat from its moorings and towed it away.

The Parliamentarians eventually breached the castle walls with powerful cannon and after a short battle in which Sir Nicholas Kemeys was killed, the garrison surrendered. A memorial tablet erected in 1935 by his descendants can be seen in the inner courtyard to mark the spot where this gallant commander was cut down at the head of his men.

Marten’s Tower at the south-east corner of the lower bailey was built by Roger Bigod, at the end of the thirteenth century. It is named after Henry Marten, one of the fifty nine  signatories to the death warrant of Charles I and when brought to trial at the Old Bailey for his part in the Civil War he was sentenced to be hanged. However,the House of Lords reduced this sentence, to perpetual imprisonment. After being confined in the Tower of London, Marten was brought to Chepstow Castle, where he was kept from 1668 to 1680.

He actually had a good life here, imprisoned with his wife for company and servants in attendance. The tower contained several rooms with fireplaces, large windows and an elegant chapel. Not only was he allowed to receive visitors, but he was able to go out to the homes of his friends in and around Chepstow. 

Living to the age of 78 he died after a stroke while eating his dinner and was buried in the chancel of St Mary’s Priory Church, Chepstow. There is an epitaph on the slab covering his tomb and the initial at the beginning of each line spells Henry Marten. Apparently he composed the verse himself in readiness for his demise, with a space left for the insertion of the date of his burial.

In the 18th century the Reverend Thomas Chest, a rather bigoted vicar objected to Marten’s monument being so close to the altar, so his remains were moved to near the west entrance of the church.

Below the depths of Marten’s tower is a dark green dungeon where Charles I’s chaplain, Jeremy Taylor was imprisoned in 1665 for alleged conspiracy in a Royalist plot. 

 The garrison was disbanded in 1685 and the castle left to decay for two hundred years. Then by the late 18th century the ruins were starting to attract visitors on the ‘Wye Tour’  who came down the river on boats from Ross-on-Wye.  It was placed into State care in 1953 and since 1984 has been in the care of Cadw (Welsh Historic Monuments).