Raglan Castle's construction, as it is seen today, was begun by Sir William ap Thomas. Located between Abergavenny and Monmouth in south Wales, the castle was built in the fifteenth century and much of it still remains. William ap Thomas had fought at Agincourt beside King Henry V and was knighted by Henry VI. He was known as the 'blue knight of Gwent'. Sir William married Elizabeth Bloet who had inherited the site on which the present castle stands from her father. It is thought that the site originally consisted of a motte and bailey castle and that the Bloet family had a manor house there. The castle has a large six-sided tower known as the 'Yellow Tower of Ghent' due to the colour of its stone. The tower is surrounded by its own moat and accessed via a drawbridge. When Elizabeth died in 1420, Sir William was able to maintain possession of the castle by an agreement with his stepson. Sir Sir William died in 1445 and his eldest son, William Herbert, carried on the building work. William was a Yorkist supporter and created Earl of Pembroke. He was executed after defeat at Edgecote in 1469.
King Charles had been staying at Raglan Castle but the fall of his support in the south west meant that he was not safe there. Charles decided to move north to meet Montrose who he believed was marching south from Scotland. Charles was unaware of Montrose's defeat at Philiphaugh on the 13th. Charles reached Chester which was held by the Royalists but under siege and entered the city. An attempt to free the city failed and Charles abandoned the city and headed for Newark.1