Chepstow Castle is amongst the most historically important fortified structures in the UK, and the oldest surviving of those built after the departure of the Romans - work started the year following the Norman invasion, 1067, under the supervision of William FitzOsbern, 1st Earl of Hereford, and the building was expanded and augmented regularly up until the seventeenth century.
The castle has an imposing location on top of a sheer, 100 foot cliff of greyish-white limestone, on the west bank of the River Wye, towards the north side of the compact town centre of Chepstow; the dramatic setting is best appreciated from the opposite side of the river, reached by a narrow bridge, at the site of a crossing point that has been in use for many centuries. The exterior can be viewed close up free of charge since the castle is partly surrounded by public parkland, while the interior, comprising various towers, courtyards and rooms, is open for a moderate fee.
The castle is served by a small car park along Bridge Street, close to the river. From here a short path leads to the main entrance, the outer gatehouse, at the east end, while another follows beneath the south-facing walls, which are some way above ground level, on top of a steep grassy bank, originally the castle motte. The path passes six towers, the last of which marks the west end of the building; near here another short path climbs slightly to a rocky area beneath the upper gatehouse, now permanently closed. All of the north wall of the castle is built directly along the cliff edge hence is completely inaccessible from the outside. The whole structure is unusually narrow in outline, being about 750 feet long but at most 150 feet across - widest at the east end, tapering towards the west.
The outer gatehouse, flanked by two wide, circular towers, leads to the lower of three baileys (enclosed courtyards), to the right of which, originally on two levels, is the main group of enclosed rooms, which include the kitchen, cellar, latrine, and the great hall. Until quite recently the gatehouse was still guarded by its original wooden doors, first installed in the 12th century, but these are now located in the exhibition hall. A low wall separates the courtyard from the middle bailey, on a higher level, which lacks a northern wall and so extends right to the cliff edge. Rising high above is the Great Tower, the oldest part of the fortifications, dating from Norman times. This is the tallest and most prominent section of the structure when viewed from across the river. The majority of the remainder of the surviving walls were constructed in the 13th century, though sizeable sections bordering the lower and middle baileys are much more recent, finished in the 1600s. A narrow gallery runs past the great tower to the upper bailey, and finally a gate and steps lead to smaller enclosure, the barbican, which adjoins the south tower and the upper gatehouse.