“The towne of Chepstow hath bene very strongly waulled,” says Leland. “The waulles began at the ende of the great bridge over Wy, and so cam to the castel, the which yet standeth fayr and strong.” To all appearances, as seen from the further side of Wye, it is strong still, and fair it certainly is, standing high upon the red cliffs that add so much to the beauty of this last bend of the river. It covers three acres of ground, but as it is built in a succession of courts, sloping upwards one above the other, the whole of its great length may be seen at once and the effect is very fine. This castle, since it was built by William FitzOsborne, Earl of Hereford, soon after the Conquest, has seen a good deal of life, and even more of death. Its second owner forfeited it, being of too independent a temperament to please the King. William, having safely imprisoned this rebellious Roger, sent him as an Easter gift his own royal robes—an attention that was meant well, but was not very tactful. Earl Roger “forthwith caused a great fire to be made, and the mantle, the inner surcoat of silk, and the upper garment, lined with precious furs, to be suddenly burnt.” This was his last act of rebellion. “By the brightness of God,” exclaimed the flouted King, “he shall never come out of prison as long as I live!”
Later on the castle passed to the great house of Clare.
“From Chepstow’s towers, ere dawn of morn,
Was heard afar the bugle-horn;
And forth in banded pomp and pride
Stout Clare and fiery Neville ride.”[13]
The greatest of the Clares, Richard Strongbow, sometimes called the Conqueror of Ireland, was born at Chepstow; “a man tall in stature,” we are told, “and of great generosity, and courteous manner.... In time of peace he was more disposed to be led by others than to command,” but “the post he occupied in battle was a sure rallying-point for his troops.”
The castle passed from hand to hand through the stirring centuries that followed Strongbow’s day. In the Civil War it had many adventures. It held for the King at first, was taken by the army of the Parliament, and was recaptured by a handful of Royalists under Sir Nicholas Kemys, by guile rather than by force. “On the whole,” says Carlyle, “Cromwell will have to go.... Let him march swiftly!” He marched swiftly and took the town of Chepstow, but besieged the castle in vain. Carlyle tells the tale in few words: “Castle will not surrender,—he leaves Colonel Ewer to do the Castle; who, after four weeks, does it.” It was not easily, however, that Colonel Ewer “did it.” The garrison, reduced to nineteen, held out till they were starving, and even then determined, not on surrender, but on flight. Their boat lay ready beneath the walls, waiting for the darkness. But when night came no boat was there, for a soldier of the Parliament, a man of keen eyes, had detected both the boat and her object, and, with a knife between his teeth, had swum across the Wye and cut the rope that moored her to the river-bank. The next day the nineteen Royalists surrendered. Thus Colonel Ewer “did the castle.”
During the Commonwealth Jeremy Taylor, the author of “Holy Living and Holy Dying”—according to Coleridge the most eloquent of divines—was imprisoned in Chepstow Castle as a follower of Archbishop Laud: and here, too, when Cromwell’s day was over, Sir Henry Marten, the regicide, suffered a mild form of imprisonment for twenty years. He was allowed not only to receive his friends but to visit them, and he was not deprived of the companionship of his wife. From what I read, however, I cannot assure myself that he appreciated the last of these privileges. He was buried in Chepstow Church, under an epitaph that he composed himself—a rhyming epitaph of a high moral tone. Yet neither poetry nor morality was Marten’s strong point. At a later date a loyalist vicar removed from the chancel to the nave the bones of the man who had signed Charles I.’s death-warrant.