History
Pickering Castle was built between 1069 and 1070 by William the Conqueror in the aftermath of the Norman Invasion to help control Northern England after the Harrying of the North. The original castle was a traditional motte and bailey castle, popular with the Normans, and made of earth and timber. There was a pre-Conquest settlement at Pickering before 1066, which was held by Morcar, Earl of Northumbria.
Architectural evidence suggests that the first part of the castle to be built in stone was the Old Hall, constructed in the 12th century. Pipe Rolls indicate that near the end of the 12th century, during the reign of Henry II, work was carried out on the bridge to the inner bailey and likely the construction of the curtain wall of the inner ward and the Coleman Tower. It's also possible that the Keep atop the motte was replaced with a new stone Keep at this time, as Henry had already done at nearby Scarborough Castle.
In 1201, King John visited Pickering Castle. He also carried out building at Pickering between 1207 and 1210, with more work on the bridges and possibly the staircase leading to the Keep.
A third building phase was undertaken between 1218 and 1236, during the reign of Henry III, due to new threats from France and some disgruntled northern Barons. The castles of Pickering, Scarborough, and York made a triangle of defense, securing the coast and eastern Yorkshire. During this period, Geoffrey de Nevill, Sheriff of Yorkshire, carried out improvements to the castle. The rampart walls surrounding the inner ward were reinforced, and the chapel was added to the inner ward. The outer shell of the Keep was enhanced, and the new Hall in its earliest form also dates from this period.
The outer ward walls remained timber until the 14th century; the wooden palisade walls were capped with pointed stakes called herisson.
In 1255, the castle was taken out of the control of the sheriff and placed in the care of the Justiciar, Hugh Bigod, who held the castle until he died in 1266. Hugh sided with the King and against Simon de Montfort and the Barons during the Second Barons' War. He kept both Pickering Castle and Scarborough Castle well defended during that uprising.
In 1267, Henry III granted the Honour of Pickering and the castle to his younger son, Edmond Crouchback, as part of the settlement when he was created Earl of Lancaster. In 1296, Edmund died, and his son Thomas, Earl of Lancaster, inherited Pickering Castle. Thomas was among the Barons who opposed the rule of his cousin, Edward II. In 1312, Thomas captured the King's favorite, Piers Gaveston, at Scarborough Castle, and executed him after a mock trial.
In 1314, Thomas improved the castle by carrying out work on the New Hall and maintained a garrison at the castle. Thomas refused to support Edward II when Edward was in Scotland at the Battle of Bannockburn. In 1321, Thomas declared open rebellion against the King. Thomas was defeated at the Battle of Boroughbridge and held as a prisoner at his own castle at Pontefract. In March of 1322, he was executed on a nearby hill, reminiscent of the treatment he had given to Piers Gaveston. After which, Edward II seized all Lancastrian lands, including Pickering Castle.
In the summer of that same year, Robert the Bruce invaded northern England, where he burned the town of Ripon and established a base at Malton, where his army carried out raids in the surrounding area. Pickering Castle and the town were spared after agreeing to pay a substantial sum of money and provide three hostages to support the Scots.
After the Scottish army returned to Scotland, Edward II appointed a new constable at Pickering Castle, John de Kilvington, and instructed him to strengthen the castle's defenses. A new drawbridge was added at the entrance to the inner ward, and a fresh supply of munitions was obtained. The garrison was also strengthened. King Edward II spent three weeks at Pickering Castle in August of 1323. The entire herisson stockade surrounding the outer ward was replaced with stone, and Rosamund's Tower with a postern gate was built behind the motte.
With the King's downfall in December of 1326 and murder in 1327, Pickering Castle returned to Lancastrian ownership and Henry, the Younger brother of Earl Thomas and subsequent Dukes of Lancaster. In 1399, Henry Bolingbroke, son of John of Gaunt, returned to England after being banished by King Richard II (his cousin), while Richard was in Ireland. Bolingbroke landed at Ravenspur and traveled to Pickering Castle to claim his estate as Duke of Lancaster. Henry Bolingbroke quickly gained support and claimed the throne of England as King Henry IV, following Richard's forced abdication. Richard II was held prisoner at Pickering Castle in 1399 until he was taken to Pontefract Castle, where he would meet his end.
King Henry IV conferred the Duchy of Lancaster, including Pickering, to his son, Henry of Monmouth, the new Duke of Lancaster and future King Henry V. Pickering Castle would remain under the Duchy of Lancaster for the next 300 years, where more repairs were carried out, including new stables built in the outer ward in the 15th century.
Pickering Castle somehow remained largely unaffected during the Wars of the Roses and the English Civil War, though the castle was held for King Charles I during the Civil War and was breached on the west side. Parts of the castle were stripped from the towers to provide more defenses for Scarborough Castle. At that time, the only serviceable building at Pickering Castle was the Mill Tower as a prison and the chapel, which was used as a courthouse.
In the early 19th century, Pickering Castle was placed in the care of the Office of Works (now English Heritage), and the chapel was restored.
Castle Highlights
Pickering Castle remains a romantic ruin with wild flowers growing from the curtain wall of the outer ward. Most of the castle is surrounded by thick trees, so it's hard to get a sense of the scale of the castle from the outside, and with just fragments of the shell-keep remaining, there is no dominant central Keep. From the approach on the outside, the remains of the Gatehouse, two towers, and southern rampart wall are visible. But once inside, the castle towers and walls are substantial.
The motte and shell-keep dominate the central area of the castle, but not much remains of the Keep. The chapel is the only completely restored building (besides the modern ticket booth and gift shop).
Three of the towers along the outer ward are still mostly intact and provide a good indication of the defenses once utilized at the castle. The Diate Hill Tower to the right of the Gatehouse is the most well-preserved, while the Mill Tower to the left of the Gatehouse was used as a prison and is said to be haunted by the ghost of a monk.
Rosamund's Tower, behind the motte hill, also includes the postern gate, used as a secret exit in times of siege. And nearby, the ruined foundations of the Great Hall and Constable's Lodging can be seen in the inner ward.
Although Pickering Castle is mainly surrounded by dense woodland, there is a path that leads around the outside of the castle, which provides great close-up views of the walls and towers. It is well worth a walk around the outside perimeter of the castle.
Pickering Castle can be thoroughly explored in two to three hours. To make a full day of visiting castles, you can combine a trip to Helmsley Castle to the east, or Scarborough Castle to the west.
Pickering Castle is also haunted.
