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There has been a settlement in Whittington since prehistoric times, and this would have almost certainly have involved some sort of defensive structure. Recent archaeological work seems to confirm this, uncovering a series of ditches and banks that probably date back over 2000 years.
Historical records suggest that there were forerunners of the present castle around in the 8th and 9th centuries, but there is little substantial evidence to support this.
There is no mention of the castle in the Domesday Book of 1086, but the village of Whittington is described in some detail, suggesting that Whittington Castle had not been built by this time.
The Normans were responsible for building the first substantial fortress on the site, presumably sometime after 1086. The first distinct mention of the castle is in 1138, when it was owned by William Peverel, who supported Empress Matilda in her long-running battle for the English Crown against King Stephen (1135-1154). The castle that Peverel built probably replaced an earlier timber structure. Stephen's successor (and Matilda's son) Henry II then seized the castle and later handed it over to the Norman Roger de Powis. In 1173 Roger de Powis was given a grant towards the cost of repairing the castle by Henry II.
On the death of William Peverel, the castle passed to his son Pain Peverel, who in turn left it to his son William. William had no male heir to his estate as he only had two daughters. His eldest daughter Mellete inherited the castle on his death. A tournament was held to determine the husband of Mellete and Warine de Metz was the victor. He was succeeded by Fulk Fitz Warine, his son, who was knighted by Henry the First.
In trying to secure his inheritance, Fulk Fitz Warine was declared an outlaw and some say his story provided the basis for the Robin Hood legends.
After Fulk the First's death, his son sought to prove the family claim on Whittington Castle. However, despite winning a court judgement in 1195, Fulk II wasn't able to take possession of the castle - dying before he was able to take up residence.
The Fulk Fitz Warines had a turbulent relationship with the English monarchy and in 1200 Fulk Fitz Warine III led a rebellion against King John and he was forced to flee to France to escape certain death. Fulk Fitz Warine was eventually granted a pardon and King John granted Whittington Castle to the family in 1204.
Fulk III later became a leading figure amongst the barons who forced King John to sign the Magna Carta in 1215. The Magna Carta, meaning Great Charter, lessened King John's powers over his barons and gave them a greater say in the government of England.
The Fitz Warines' strained relationship with the monarchy led King Henry III to ensure that Whittington Castle was no stronger than was necessary to see off the Welsh. Henry was obviously concerned that the castle might once again be pitted against the English Crown.
In 1221 the Earl of Chester received authority to strengthen the castle. In 1223, the castle was abandoned before being besieged by Llywelyn ap Iorwerth of Gwynedd who was expanding his empire into Powys and the Welsh marches. After a brief period of occupation by the Welsh, the castle was almost completely rebuilt .The inner bailey was raised, and fortified with substantial walls and imposing towers. This castle boasted seven towers, walls almost four metres thick and a massive 42 foot long drawbridge.
Whittington Castle was granted by King Henry III to Llewelyn ap Gruffudd in 1265, along with several other border strongholds. Custody of the castle was held by Hamo Le Strange as Fulk V was only a minor.
The next Fulk became a famous warrior, fighting and dying (by drowning) in the battle of Lewes, Sussex in 1264. He left a son and heir, and a daughter called Eve. Following, the defeat of the Welsh Princes in the 1280s, the castle was restored to the Fulk-Warines. Whittington became a far more peaceful place to live and the castle's role started to reflect this.
A succession of Fulks followed, one of which was also a warlike warrior, who attended the Black Prince (Prince Edward of Wales, son of Edward III) into Gascoigne and the Earl of Warwick into Flanders (1345), amongst other places.
This Fulk expressed a wish that upon his death he be buried in the chancel of the church at Whittington. It is rumoured that his remains, found in an Oak coffin three inches thick, were found in the porch of the present St. John the Baptist church in the eighteenth century.
In 1407 Fulk X died and the castle was taken over by the King. In 1420, Fulk XIV died aged only 14. He was succeeded by a sister and so the Fulk Fitz Warine line at Whittington came to an end.
Whittington didn’t officially become part of Shropshire until 1536, through the Act of Union, which abolished the Marcher lordships. In 1545 the castle was sold to the Crown and a Crown Survey acknowledged the onset of structural decay at the castle, which has worsened over the years.
The early 17th century saw much of the stone from the castle being removed to build ironworks, houses and even roads. Its owner in the 1620’s was Francis Albany, who received permission to sell off stone from the castle to help pay his considerable debts.
During the English Civil War the dilapidated castle was held for the King and was partially destroyed by the cannons of the opposing parliamentary forces in 1643.
In 1673 the castle was leased to Thomas Lloyd, a London merchant, who undertook repairs of the castle buildings.
At the time of Queen Mary II (1689 – 1694) ownership of the castle was granted to Fitz-Alan, Earl of Arundel.
In around 1760 the eastern tower of the inner bailey collapsed into the moat, as a result of frost damage, and soon after much of what remained of the bailey was used to repair local roads and build houses.
Whittington remained a manor house until the 19th century, although its downfall has been fairly constant since the 17th century. Eventually an owner willing to look after the ruins arrived on the scene. In the first years of the 19th century, William Lloyd funded a restoration programme that saw the gatehouse rebuilt into what it is today. The castle owes much of its present condition to restoration works in the 1960’s.
The Whittington Castle Preservation Trust was established in 1998 with the aim of halting the decline. In 2002 they were granted a 99 year lease with a view to protecting the castle’s future.