It is thought that there has been a settlement at the point on which the castle sits for over 3000 years. Early castles had been built due to its defensive position due to being surrounded by treacherous and energy sapping marshlands. A Norman motte and bailey castle was built by William Peverel (c1050-1115), a Knight thought to have fought at the Battle of Hastings. His eldest daughter Mellet inherited the castle and married into the Fitzwarines family after her hand in marriage was won in a tournament, the family keeping the castle until around 1420. During the civil war it was loyal to the Royalists until Oliver Cromwell's Roundheads took it by force in 1643. At the time of Queen Mary II ownership of the castle was granted to Fitz-Alan, Earl of Arundel. Later it was sold to Francis William Albany Esq., a London merchant. When his granddaughter Sarah married Thomas Lloyd Esq of Aston the two estates were united. Today the castle is managed by the Whittington Preservation Trust. There are a number of myths and legends connected with Whittington and the Castle. The most obvious is that of "Dick Whittington". There are similarities between Dick Whittington's coat of arms to that of Fouke Fitswarine who had a hand in building Whittington Castle and lived in a cottage not far from the castle. Another legend is that of Robin Hood. There are many similarities between the lives of Fouke Fitswarine and Robin Hood which suggest that the two characters may have similar origins within our oral tradition. In the ruins it said that people have seen and heard two children peering out of t he twin towers, the tale saying that these are past heirs of the castle. When a cursed Elizabethan chest belonging to the castle was opened, apparently the heirs perished in great pain. Indeed, so much fear and superstition surrounds this chest that it has been hidden away for many years, until recently taken to a secret location for restoration. There are many eye witness accounts of paranormal activity at the castle. Gardeners have reported seeing strange white mists and balls of light appearing from nowhere and feelings of being observed. Simlar phenomena has also been reported by the night watchman, inlcuding that of seeing a lone horseman in ancient apparel. Loud, eerie and unexplained voices have also been heard coming from the locked castle tower.

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