From Classic Encyclopedia 1911
CHEPSTOW, a market town and river-port in the southern parliamentary division of Monmouthshire, England, on the Wye, 2 m. above its junction with the Severn, and on the Great Western railway. Pop. of urban district (Igor) 3067. It occupies the slope of a hill on the western (left) bank of the river, and is environed by beautiful scenery. The church of St Mary, originally the conventual chapel of a Benedictine priory of Norman foundation, has remains of that period in the west front and the nave, but a rebuilding of the chancel and transepts was effected in the beginning of the 19th century. The church contains many interesting monuments. The castle, still a magnificent pile, was founded in the 11th century by William Fitz-Osbern, earl of Hereford, but was almost wholly rebuilt in the 13th. There are, however, parts of the original building in the keep. The castle occupies a splendid site on the summit of a cliff above the Wye, and covers about 3 acres. The river is crossed by a fine iron bridge of five arches, erected in 1816, and by a tubular railway bridge designed by Sir Isambard Brunel. There is a free passage on the Wye for large vessels as far as the bridge. From the narrowness and depth of the channel the tide rises suddenly and to a great height, forming a dangerous bore. The exports are timber, bark, iron, coal, cider and millstones. Some shipbuilding is carried on.
As the key to the passage of the Wye, Chepstow (Estrighorel, Striguil) was the site successively of British, Roman and Saxon fortifications. Domesday Book records that the Norman castle was built by William Fitz-Osbern to defend the Roman road into South Wales. On the confiscation of his son's estates, the castle was granted to the earls of Pembroke, and after its reversion to the crown in 1306, Edward II. in 1310 granted it to his half-brother Thomas de Brotherton. On the latter's death it passed, through his daughter Margaret, Lady Segrave, to the dukes of Norfolk, from whom, after again reverting to the crown, it passed to the earls of Worcester. It was confiscated by parliament and settled on Oliver Cromwell, but was restored to the earls in 1660. The borough must have grown up between 1310, when the castle and vill were granted to Thomas de Brotherton, and 1432, when John duke of Norfolk died seised of the castle, manor and borough of Struguil. In 1524 Charles, first earl of Worcester and then lord of the Marches, granted a new charter of incorporation to the bailiffs and burgesses of the town, which had fallen into decay. This was sustained until the reign of Charles II, when, some dispute arising between the earl of Bridgwater and the burgesses, no bailiff was appointed and the charter lapsed. Chepstow was afterwards governed by a board of twelve members. A port since early times, when the lord took dues of ships going up to the forest of Dean, Chepstow had no ancient market and no manufactures but that of glass, which was carried on for a short time within the ruins of the castle.