Pickering Castle stands at a natural crossing on the east-west road between marsh and moorland. A settlement at Pickering can be traced back to the 3rd century and in pre-conquest times was held by the Anglo-Saxon Earls of Northumberland.

By the late forteenth century the castle was already a dated fortress, but one whose successive owners played crucial roles in shaping the history of England.

Today the castle provides a pleasant stroll round its walls and is a good example of an early stone motte and bailey castle.

Plenty of parking is available with a short walk to the castle. The only part of the castle that involves a bit of a climb is to explore the ruined shell keep.

~ History ~

1060's ~ Pickering Castle is held by Tostig, Earl of Northumberland and brother to Earl Harold Godwinson, the most powerful man in England. Tostig's heavy handed murderous approach to his Danish and Anglo-Saxon inhabitants, whilst at the same time failing to protect his own people against raids by his friend, the King of Scotland, results in his own people rebelling. They desend on York, killing Tostig's officials and declaring Tostig an outlaw. Earl Harold is forced to meet with the rebels and so as to avoid a full blown rebellion in the North, with William Duke of Normandy threatening the South coast, with authority granted by King Edward the Confessor, exiles his own brother.

1065 ~ The Northumbrian rebels choose Morcar, brother of Eadwine, Earl of Mercia, as their new Earl. They march south to force the issue with Earl Harold who concedes to their demands.

1066 ~ On the death of Edward the Confessor, Morcar supports King Harold. However his own people are far from happy and so King Harold is forced to meet with them in York to secure their support.

Morcar joins his brother Eadwine in repulsing King Haralds exiled brother brother Earl Tostig, who is ravaging the Mercian coast.

However, Tostig later returns, this time with a great army backed by his ally King Harald Hardrada to take back his Earldom and secure the English throne for the Norwegian King.

This time Morcar and his brother are defeated in a fierce battle.

York is surrendered, and so Harold Godwinson is forced to march in haste to save the North, defeating Tostig and Harald Hardrada at the  Battle of Stamford Bridge, before being forced to march what remains of his exhausted army South, to meet Duke William of Normandy at the Battle of Hastings. Ungrateful for their deliverance, Morcar and his brother hold back their forces from joining Harold in the defence of the Kingdom against the Normans. After Harold's death and defeat at the Battle of Hastings, Morcar and his brother, having failed to secure their own King on the throne, Edgar the Ætheling, submit to William the Conqueror.

1068 ~  Morcar and Eadwine rebel against King William, but are later pardoned for their actions but sent to prison, from which both escape back to their Earldoms before this can be carried out.

Morcar joins the Anglo-Saxon rebellion in the Isle of Ely, until its surrender. He again seeks for a pardon, but this time King William ensures that there is no escape. Morcar is imprisoned for the next twenty years in Normandy and his lands, including Pickering Castle is forfeit to the Crown. William raises a new timber castle at Pickering.

1087 ~  On King William's deathbed he orders that Morcar should be released, together with others whom he has imprisoned, on condition that they take an oath not to disturb the peace. Morcar swears the oath and is released, but is almost immediately arrested on the orders of King William Rufus, who takes him to England, and upon arriving at Winchester puts him in prison from where he never returns.

1180's ~ King Henry II orders the timber defences of Pickering to be rebuilt in stone.

1201 ~ King John visits the castle, returning seven years later to check on the building work he has ordered to be completed.

1220's ~ King Henry III rebuilds and strengthens the existing walls in expectation of the Baron's rebellion as part of a protective castle chain including York and Scarborough. Despite the defensive improvements the castle is damaged during the civil war. Upon conclusion of peace extensive repairs are made.

1255 ~ The castle is taken out of the care of the Sheriff and placed into the hands of the powerful baron, Hugh Bigod.

1264 ~ Civil War breaks out between King Henry III and his barons, led by Simon de Montfort. Bigod is ordered to defend the castle of Pickering and Scarborough against the rebels.

1267 ~ Following Hugh's death King Henry III grants the castle to his youngest son, Edmund Crouchback, who does little to maintain the castle.

His son Thomas, inherits his fathers estates as Earl of Lancaster.

1312 ~ After years of plotting and scheming against his cousin King Edward II, Thomas captures the King's favourite, Piers Gaveston, at Scarborough Castle. A summary trial is completed and he is executed.

1314 ~ King Edward II leads an English army north to deal with the Scottish threat once and for all. Thomas refuses to support his cousin.

King Edward II's forces are severely defeated at the Battle of Bannockburn.

1321 ~ Thomas finally comes out in open rebellion against King Edward. He is however defeated at the Battle of Boroughbridge and imprisoned in his own castle of Pontefract, before being executed the following year, as he had done to Piers Gaveston.

1322 ~ King Edward again marches north into Scotland, provoking Robert the Bruce to invade northern England. Pickering Castle and town are saved by the promise of three hostages, including the castles constable, and a substantial sum of money. Upon the Scots withdrawing King Edward installs a new constable to make repairs to the castle and build a new curtain wall, towers and gatehouse.

1323 ~ King Edward spends three weeks at the Castle to inspect progress.

1326 ~ Following King Edward's capture, imprisonment and murder at Berkeley Caste, Pickering Castle is returned to Lancastrian ownership.

1398 ~ Henry Bolingbroke, son of the Duke of Lancaster and owner of Pickering Castle, is banished on the orders of his cousin King Richard II, for conspiring with his enemies whilst the King was absent in Ireland.

1399 ~ Henry returns and quickly gains support, heading to Pickering Castle to claim his ducal estates. His support multiplies sufficiently to press home his claim to his cousins throne. King Richard is forced to abdicate. Henry is crowned King Henry IV of England.

Pickering Castle, now an ancient fortress, is left to slowly fall into ruin.