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Robert D'Oyley of Liseux built Wallingford Castle, a motte and bailey affair, between 1167 & 1171. He spent much of his time acquiring land, mostly at the expense of the church. The monks of Abingdon were eventually forced to conspire against him and pray for his repentance. He fell ill and was warned in a dream to mend his ways. Afterwards, he began endowing many churches and monasteries, including Wallingford Priory. D'Oyley's daughter married Brien FitzCount, the unwavering follower of the Empress Matilda in her struggle with her cousin, Stephen, for the English throne. He was one of only two landed lords to immediately join her cause. In 1141, Matilda had to make a daring escape from the besieged Oxford Castle. She slipped out at night and abseiled down the castle walls with only three loyal knights. Dressed in white, they made their way through the snow covered countryside, crossed the frozen Thames on foot at Abingdon, then by horse to Wallingford and safety. People who saw them in the night thought they were ghosts! Later, when Matilda's son, the Henry II-to-be, arrived in the town, the two sides negotiated and signed the peaceful Treaty of Wallingford (1153) by which it was decided Henry would succeed to the throne after King Stephen's death.
The castle later expanded and gained high stone walls, and also town walls atop the Saxon banks. Prince Richard, Earl of Cornwall & Holy Roman Emperor held the castle for much of the reign of his brother, Henry III. He spent a fortune on lavish entertainment and building works, making Wallingford his favourite home. Then, when he almost drowned at sea, he swore to spent all his money on the church. He is quoted as having said, "Would that it had pleased God that I had expended all that I have laid out in the Castle of Wallingford in as wise and salutary a manner". In 1335, the castle was granted to the Black Prince, and it was his principal residence, when he was in the country that is. His wife, Joan the Fair Maid of Kent, died of a broken heart at Wallingford, when her son, Richard II, condemned his half-brother, John Holland, to death for the accidental murder of a court favourite. In the end the unfortunate Holland was given a reprieve, but it was too late for poor Joan. Her will was written at Wallingford and she may have been buried in the Priory, though other sources say her body was taken to Stamford (Lincs). The hated Piers Gaveston, favourite of Edward II, was made Lord Wallingford in 1307 and given the castle for services rendered. He is noted for holding a magnificent tournament here which all the nobles of the land were obliged to attend. Fair Katherine, Queen of Henry V, retired to Wallingford after her husband's death. Her son, Henry VI, was educated here, and it was at the castle that the Queen was seduced by his squire, Owen Tudor. Owain's father was a cousin of Owain Glyndwr (Prince of Wales) and his paternal grandmother was 4x great grandaughter of Gryffydd ap Lord Rhys, the last King of Deheubarth (South Wales). Together they became the grandparents of King Henry Tudor.
The castle ruins stand today within a lovely walled park, created by the Borough Council, off Castle Street. There is little in stone to see except the remains of the tower of St. Nicholas' Collegiate Church which stood within the castle walls. Climb the motte and you can see the footings of some more walls with two small sections in the fields to the north. The whole is very well laid out and you get a fine view of the town.