The castle keep was originally built in the 12th century as a stronghold of the Neville family and it was to here that Richard of Gloucester was sent to learn how to be a knight. It was here that he met his future wife, Anne, daughter of his cousin, Richard Neville, Earl of Warwick, also known as the Kingmaker. In later years, when Richard was given the governance of the north of England by his brother, Edward IV, it was his favourite residence. It was here that his son, Edward of Middleham, was born in 1476 and died in 1484.

Although ruined, much still stands, especially the curtain wall and the keep with the great hall. There is a stairway that can be climbed to get views of the surrounding countryside. Nearby is the Prince's Tower, so-called because the young Edward lived there.

A few years ago, a rather controversial statue of Richard III was erected in the bailey, close to the entrance. The sculptor, Linda Thompson, has tried to portray various descriptions of Richard, including the good king and the Shakespearian villain. A basilisk is partially visible behind Richard, its tail curling over his right shoulder to form part of the livery collar.

The church at Middleham, dedicated to St Akelda, a saxon woman murdered for her beliefs, was embellished by Richard III. It was here, in 1477, that he founded a college, where priests were endowed to say masses for the House of York. Richard’s college did not survive his death, but a college of canons under a different statute did continue, and was only brought to an end in the Victorian period. One of the last of these canons was the author Charles Kingsley. Buried in the church is the author and playwright Caroline Halstead who wrote an early biography of Richard III.

The church has been the recipient of several gifts from the Richard III Society (or it’s predecessor, the Fellowship of the White Boar), with a stained glass window portraying Saints Richard and Anne, and a heraldic altar frontal, bearing the Plantagenet and Neville arms. Also in the church is a replica of the Middleham Jewel, the original being in the Yorkshire Museum. It was found nearby to the castle and may have been the property of Richard or a member of his close family.