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Robert D'Oyley of Liseux built Wallingford Castle, a motte and bailey affair, between 1067 & 1071. 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 Brian 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 and the castle became one of her main strongholds in the south of England. FitzCount kept a special prison there which he called the 'Cloere Brian'. This was named after a bag for holding a hammer, since the Royalist commander, William Martel (whose surname means 'hammer'), was imprisoned and tortured there until his family purchased his release.

In 1141, Matilda herself had to make a daring escape from her besieged headquarters at Oxford Castle to Wallingford 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! Wallingford Castle was subsequently placed under three separate sieges in order to try and check its constant raids on the lands of King Stephen's supporters. For the Second Siege, the Royal forces built themselves a castle across the river in Crowmarsh Gifford (Oxfordshire) to use as base. There were others at Brightwell, South Moreton and Reading, but these were soon destroyed. However, it was the Third Siege of Wallingford Castle in 1152 which became the most serious thread. The King's men took both the bridge and the town and besieged the castle for a year before Matilda's son, Henry, the Duke of Normandy, arrived to relieve the garrison. King Stephen then moved to lead his troops in person but peace terms were agreed and the two sides withdrew. It was this meeting which eventually led to the signing of the Treaty of Wallingford at the castle and the end to the Civil War, as Henry (later King Henry II) was accepted as Stephen's heir.

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".

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, even though they couldn't stand him. After Gaveston's execution in 1312, the King gave Wallingford Castle to his wife, Queen Isabella. Ten years later, Lords Audley and Berkeley were imprisoned there for their part in the Earl of Lancaster's rebellion, but the castle was attacked by the De La Beche family and other adherents of the Earl, and the two escaped. For a time, Queen Isabella used the castle as her headquarters during her rebellion against her husband. After the King's capture and imprisonment, she spent Christmas 1327 there, celebrating with her lover, Mortimer. Upon her son's establishment of control of the country, however, it became a lonely retreat for her retirement from public life. 

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 most sources are clear that her body was taken to Stamford (Lincs) to be buried alongside her first husband. In 1381, Richard of Wallingford, the castle's constable, was one of Wat Tyler's deputies during the Peasants' Revolt. Though the rebellion as a whole was not that popular in Berkshire.

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). At the close of the War of the Roses, Henry VI's capable wife, Queen Margaret, was imprisoned at Wallingford Castle. The Lancastrian cause seemed lost until Katherine and Owen's grandson managed to take the Throne as King Henry Tudor. 

During the Civil War, Wallingford Castle was fortified for the King and two heavy cannon were stationed in the town. It was the third to last Royalist stronghold in the whole country to fall and , only then, after Colonel Blagge had held out against a Parliamnetrya siege for some sixteen weeks. In 1652, the Council of State ordered it to be totally demolished. 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.

The following were born at Wallingford Castle:

• Prince Richard of Cornwall, b.1246, son of Prince Richard, Earl of Cornwall & Holy Roman Emperor

The following died at Wallingford Castle:

• Prince William, Count of Poitiers, d.1156, aged 2, eldest son of King Henry II
• Prince Richard of Cornwall, d.1246, aged 1 month, son of Prince Richard, Earl of Cornwall & Holy Roman Emperor
• Princess Joan of Kent, d.1385, wife of Prince Edward "The Black Prince", Prince of Wales, mother of King Richard II & daughter of Prince Edmund of Woodstock, Earl of Kent