Chepstow, alias Striguil, was the earliest and the most important of the original bases from which the Normans conquored South Wales. the first foothold occupied beyond the old Anglo-Saxon border. It is a lofty but very narrow castle, occupying the whole backbone of a rocky spur which has the precipitous cliffs above the Wye on one side, an a deep and steep ravine on the other, separating it from the hill on which Chepstow town stands.

It may be taken for granted that the original fortress of William Fitz Osbern was on the central summit of the spur, where the present Norman keep stands, and that the keep itself was built some fifty years later, either by Walter de Clare, to whom Henry I. gave the lordship of Striguil about 119, or by his nephew and successor, Richard de Clare, Earl of Pembroke, the famous "Strongbow,'' the conqueror of Ireland.
This keep no doubt replaced the original wooden "tower of strength,'' put up by Fitz Osbern. The present middle ward, sloping down from the keep toward the Wye, would represent the outer bailey of the first castle. There are traces of a deep-cut ditch between it and the much later outer ward: while on the other side of the keep, to the north, the present upper ward probably represents a second and smaller ``bailey.'' It is separated from the plaform of the spur northward by another very deep ditch.
Presumably, then, the keep with a bailey on each side of it, was the castle as it existed when Walter de Clare dwelt there in the days of Henry I. Walter lived long, died in 1138, and passed Striguil on to his nephew ``Strongbow,'' who held it till his death in 1176.
The Conqueror of Ireland, as everyone knows, died not long after his installation as Lord of Leinster, leaving only one daughter, Isabel, by his wife Eva, the heiress of Dermot Macmorrough. The child was but three years of age, and it was not till thirteen years after that Richard I. gave her hand to William the Marshall, one of his companions of the Crusade, who assumed in her right the title of Pembroke, and became lord of Striguil, as well as of Pembroke and Strongbow's Irish lands.
The Marshall, the victor of Lincoln, and the saviour of the crown of the infant Henry III, dwelt much at Chepstow, and undoubtedly he or his sons stand responsible for the enormous extension of the castle downhill, toward the river, and uphill, along the top of the spur, beyond the small original northern bailey. Downhill the extension consisted of the present lower ward, running quite close to the bank of the Wye, and presenting a tremendous front of defence, the heavy gate-house, with its two drum-towers, and the portcullis chamber between them.
This sufficiently formidable work was strengthened later, by the throwing uot of a round corner tower, with a ``spur'' at the exposed south-east angle of the ward.
At the other, or upper, end of the castle, the thirteenth century builder-- one cannot besure which of the Marshall earls it was--fortified the original smaller bailey with good walls, so as to make it an integral part of the fortress, and threw across its outer ditch a ``fore-building'' or barbican, only to be reached by a drawbridge. This was the castle's back door into the open country; it was no mere trifle, with a strong and lofty gate-house of its own.
Such large additions having been made to the fortress, it was possible to alter its internal arrangements. The keep, which must originally have contained most of the living-rooms, was turned into a single great dining-hall, with a ``solar'' or retiring room for the lord and his family at its upper end. The boundary between this chamber and the main hall devoted to the retainers, is obviously indicated by a decorative arch four-fifths of the way up the hall. Meanwhile the new lower ward was given spacious living-rooms and dormitories, of good thirteenth century architecture, with a kitchen suite on its river side, and a large square tower, containing a chapel and many good chambers, on its inland side.
On the death of Earl Ambrose, last of his line, in 1145, the vast Marshall possessions in England, Wales and Ireland, were divided among his four sisters. Maud, the eldest, got Striguil and its ``Honour of Nether Gwent'' as her portion, and also took the dignity of the Marshalship of England to her husband, Hugh Bigod, Earl of Norfolk. Severed from all the other Marshall lands, and united to those of a great earl whose main interests lay in East Anglia, Striguil ceased t be a centre of a principality, and became only an outlying possession of the Bigods. A couple of centuries were to pass before it became again the chief residence of its master.
From the Bigods Chepstow passed to Thomas of Brotherton, the younger son of Edward I., whose heiress took it to the Mowbray dukes of Norfolk. In 1468, Duke John, last of that line, feeling, as it would seem, no great interest in the place, disposed of it by a great exchange of lands to William Herbert, first Earl of Pembroke of that name, the favourite of Edward IV., who was busy in accumulating South Welsh estates on every hand. Earl William perished for the House of York--beheaded by the rebel ``Robin of Redesdle,'' after Edgecot Field. His son andsuccessor left an only daughter, Elizabeth Herbert, who was married by Henry VII. to his only male kinsman on the mother's side, Charles Beaufort, alias Charles Somerset, the one Beaufort who came alive through the Wars of the Roses. Charles was illigitimate--the son of that Duke Henry who perished after Hexham Field. But his cousin, the king, made much of him, and gave him the hand of this great Yorkist heiress. He repaid these bounties by much good service, as soldier, admiral and diplomatist. Henry would have liked to have given him the title of Earl of Pembroke, but this had to be returned to its old Lancastrian owner, Jasper Tudor. So he was given, instead, some years after, the title of Earl of Worcester, with which Striguil (and Raglan also) have been ever since connected, though it is now swallowed up in the dukedom of Beaufort.
Martin's TowerThe Beaufort-Herbert line seem to have dweltindifferently at Charles and at Raglan, in their earlier days, and the founder of the family, Earl Charles, is buried in Charles Church. It is probable that the modernized parts of the castle, especially the handsome Tudor-windowed chambers which are imopsed upon thirteenth century walls in the lower ward, are of their construction. But Chepstow, despite of modern improvements, could not compare with the spacious and sumptuous Raglan, and the family tended more and more to reside in that mganificent building--where the great Earl of Worcester, temp. Charles I., held his almost regal court.
But Chepstow becomes prominent in history once more during the Civil Wars of King and Parliament. It was of high strategic value as covering the little port from which, despite of Parliamentary garrisons in Gloucester and Bristol, Charles I. kept up his communications between Oxford and South Wales. As long, indeed, as Bristol was held for the Parliament, it was the only way in which this touch could be maintained. This was the reason why Sir William Waller made a successful dash at it in 1643, hoping to cut the line completely. But Waller's success was transitory, and only a few months later Prince Rupert stormed Bristol, and opended the communications again. From July, 1643, to the end of 1645, Chepstow was a most important base, by which royalist supplies and troops passed freely by water to the east. After the fatal Battle of Naseby, Fairfax ordered Colonel Morgan, governor of Gloucester, to reduce Chepstow at all costs. This led to its first siege under modern conditions. Morgan brought up heavy guns and mortars, and battered the lower ward with success. A great breach was made in its curtain, whereupon the Governor, an Irish Colonel Fitzmorris, surrendered without standing a storm.
But Chepstow was to see a second siege in that ``flash in the pan'' called the Second Civil War, of 1648. South Wales was one of the main centres of revolt agaisnt the Parliament, and an enterprising royalist gentleman, owner of the neighbouring estate of Caldicot, Sir Nicholas Kemmis, seized the place by surprise, and held it against Cromwell, when the latter swooped down to suppress the insurrection (May 11).
Oliver had come in haste, without artillery, and was more anxious to beat the enemy in the open field than to take isolated castles. Accordingly he handed over the siege to Colonel Ewer, and marched on into the west. The last siege of Chepstow lasted a fortnight only: having got heavy guns from Gloucester, Ewer breached the south-western side of the lower ward, apparently the same point where Morgan has broken in there years before.
Kemmis, after a vain attempt to abscond by boats on the Wye, began to treat for terms. But he haggled too long, and Ewer, knowing that such a proposal meant tht the governor was despairing of further power to resist, would grant nothing but unconditional surrender. He broke off the negotiations, and ordered a storm. When the assailants reached the breach, the greater part of therank and file of the garrison flung down their arms; but Kemmis threw himself in the way of the enemy and was slain (May 23).
Despite of the easy way in which Chepstow had been twice taken by the force of artillery, the Parliament did not ``slight'' it, like so many other castles, but repaired the breach, and kept it as a permanent garrison, and incidentally as a state prison. In that capacity it endured many years--Jeremy Tayler was shut up there by Cromwell, and Henry Martin, the regicide, by Charled II. The latter was so long a prisoner in the rather comfortable apartments in the lower ward, that his name has stuck till this day to ``Martin's Tower.''
Chepstow ceased to be a garrison in 1690--but its old owners, the Beauforts, had little use for it; the place was simply neglected, and its buildings, which were still in good order, were let out as warehouses, workshops and meeting-rooms to townsmen of Chepstow.
An eighteenth century entrepreneur turned one block into a glass-factory, and another into a smithy. As no proper repairs were ever made, diliapidation ensued. The roof of Martins Tower fell in about 1803, and in the other chambers wind, weather and ivy roots, those destroyers of masonry, worked their united will till Victorian times. For the last fifty years the castle has been kept from further decay. Its whole outline remains intact; one can still walk wound the entire circuit of the ramparts, and Strongbow's keep, Martin's Tower, and the great gate-house are still externally strong. Though roofs and interiors are gone, Striguil can still be studied as an epitome of Marcher history and architecture.

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