Chepstow

Chepstow Castle was begun in 1067 by William Fitz Osbern, Lord of Breteuil. At that time Norman expansion into Wales was slow, possibly deliberately so. Norman control over England was effectively limited to the south-east of the country; there were rumours that the sons of King Harold were in contact with King Diarmait of Leinster, who was prepared to provide them with ships and troops to mount an invasion. The Conqueror himself was away in Normandy. Fitz Osbern chose his site for Chepstow Castle well. It sits on a long narrow ridge high above the Wye, its defensive capabilities to landward being enhanced by a ditch.
An extract from from"Down the Severn Photographic Memories".

The castle stands on a narrow ridge high above the River Wye. It was begun by William Fitz Osbern in 1067, and enlarged by its subsequent owners the de Clares, the Marshalls, the Bigods, and the Earl of Pembroke. It was held for the King in the Civil War, and after the war the regicide Henry Marten was imprisoned here for twenty years.
An extract from from"50 Classics - Castles".

In this picture we can see the remains of the two-storey rectangular fortified hall built by Fitz Osbern on the narrowest part of the ridge. It is not a keep, as its walls are only 3-6ft thick. On the left is the huge D-shaped tower built in the late 13th century by Roger Bigod III. It is protected against attack by battering ram or by undermining with spur bastions. To the right of it is the twin-towered gatehouse, which dates from between 1219 and 1245. Originally there would only have been arrowslits in its front face; the windows are from a later period. On the top of the gatehouse there would once have been a hourd, or wooden gallery, from which the castle’s archers could command the ground on the approach to the gate.
An extract from from"Down the Severn Photographic Memories".

Situated on the Wye just above its junction with the Severn, Chepstow derives its name from Chepe-stow, meaning market town. In January 1644 Edward Massey, the Parliamentarian garrison commander at Gloucester, launched a lightning raid upon Chepstow by boat; his troops captured a supply ship laden with stores for the Royalists at Worcester. The commander of the Chepstow garrison, Captain Carvine, was killed in his chambers at the George Inn.
An extract from from"Down the Severn Photographic Memories".

Until the late 13th century, the town of Chepstow appears to have had no defences on its landward side. It was then that Roger Bigod III built the town wall, which was some 1200 yds in length and had a number of semi-circular towers. The only entrance into the town from the west was by way of the town gate.
An extract from from"Down the Severn Photographic Memories".