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Raglan Castle stands on the site of a Norman motte castle of c.1070. That earlier castle survived in some form up to the early 1400s and included a lord's hall. In 1432, it became the property of Sir William ap Thomas, a Welsh knight who had fought at Agincourt (1415). It was he who started to build the structure whose magnificent ruins still dominate the landscape.
The first building was an unusual hexagonal-plan great tower, whose foundations and lowest courses of walling encase the old Norman motte. Known as the Yellow Tower of Gwent, it has three stories above the basement (and had one more before it was slighted after the Civil War, in 1646). It was built over the years c.1430?45, given combined arrow-slit and gun-port openings at ground-floor level, and was equipped with a boldly projecting machicolated parapet all round the top. The tower tapered outwards slightly from the top downwards on all six sides and, at ground level, the walls were nearly 3 metres (10 ft) thick. Each story consisted of one main room, with chambers of where needed, served by a spiral stair positioned in the walling.
Around the outside of the basement is the remnant of a low curtain wall, added in c.1450?60, also hexagonal with rounded projecting corners which were turrets with battlements, whose tops were approximately as tall as the gun-port/arrow-slit openings, enabling defenders inside the tower to give protected covering fire to other, more exposed defenders behind the battlements. This tower stood completely surrounded by its own wide and deep ditch, at first crossed by means of two drawbridges with elaborate mechanisms. on the north-west face.
When the castle was enlarged in a second building period, c.1450-69, a great gate was built, approached from outside the castle, and the drawbridges were abandoned. A new approach from the great tower into the newer parts was constructed in the form of a three storey forebuilding which led to a bridge across the moat, and which joined with the parlour/dining room block on the north-east side of the new works.
The new works were ranges of buildings round two courtyards, the Pitched Court and the Fountain Court. The principal buildings in both were of polygonal (chiefly hexagonal) plan. In the Pitched Court (north-east) the gatehouse and its adjoining huge Closet Tower (three storeys plus basement) were equipped with gun-ports and with extensive machicolation at parapet level. There are several more domestic structures including the office wing, kitchen tower, pantry, buttery, great hall and the chapel lying alongside the hall. This side of the Pitched Court was also the north-east side of the Fountain Court, so called from a marble fountain that once graced its courtyard. The court had apartment blocks on three sides and included the South Gate which is almost square, not polygonal. The base of this tower may well be a relic of the earlier castle.
Raglan Castle was held by the Somerset family who, in the sixteenth century, were Earls of Worcester. The 5th Earl, who became 1st Marquess, sided with Charles I in the Civil War, and Raglan was besieged in June 1646 by Parliament, sustaining a devastating bombardment for several weeks and surrendering in August.