Occupying a low-lying site in the Lincolnshire Wolds, Bolingbroke Castle was first raised by William de Roumare, Earl of Lincoln, during the time of the anarchy between King Stephen and his cousin Matilda. This early castle would have been constructed from timber, but little is known of its plan.

The first stone castle was built on the site during the 1220s by Ranulf de Blundeville, Earl of Chester and later Earl of Lincoln, and followed a hexagonal plan. The curtain walls had semi-circular flanking towers at five corners, and one of the earliest recorded round-towered gatehouses at the sixth. Surprisingly, Bolingbroke Castle never appears to have contained a central Keep, as was the case with many other castles of this period. The whole structure was entirely surrounded by a substantial moat with access via a drawbridge.

On the death of Ranulf de Blundeville, the castle passed through the De Lacys before coming into the possession of John of Gaunt, 1st Duke of Lancaster and his wife Blanche. They lived at Bolingbroke Castle c1360-1380, and their son Henry of Bolingbroke, the future King Henry IV, was born there in 1367.

Henry of Bolingbroke was exiled by Richard II in 1397, and the castle was subsequently seized by the crown on John of Gaunt's death. Angered by this, Henry returned from exile in France, duly deposed King Richard, and was crowned king himself on the 30th October 1399. He was never to return to Bolingbroke Castle.

The importance of Bolingbroke Castle was now on the decline and used only as an administrative centre. It never played a part in the 'War of the Roses' that raged between the houses of York and Lancaster during the second half of the 15th century. Throughout the next century the castle continued to decline and, by 1636, a survey found that it was uninhabitable.

With the outbreak of the English Civil War, the fortunes of Bolingbroke Castle were to change momentarily. Garrisoned in 1642 by the Royalist army under the command of the Marquis of Newcastle, the castle would inevitably see action once the Parliamentarian army under Cromwell and Fairfax gained the upper hand. It didn't have to wait long. On 9th October 1643, Bolingbroke Castle was besieged, finally surrendering on the 14th November the same year.

In 1652 the decision was taken to 'slight' or blow up Bolingbroke Castle, and this was completed with much severity. Inevitable robbing of the stone by the local population would soon leave very little trace of the castle at all.

A major excavation to uncover the surviving foundations of Bolingbroke Castle was undertaken in the 1960s and, with the clearing of the moat, many of the walls now stand to a reasonable height. The site passed from the care of English Heritage to Heritage Lincolnshire in 1995.