Caldicot Castle Caldicot Castle ( ) is an extensive stone medieval castle in the town of Caldicot , Monmouthshire , in southeast Wales . The castle became a Grade I listed building on 10 June 1953 . It was in the possession of Thomas of Woodstock , a son of King Edward III of England , until his death , when it reverted to the Crown . Caldicot Estate . Caldicot is mentioned in the Domesday Book of 1086 , not for its castle , but as an agricultural holding of Durand , Sheriff of Gloucester . Walter fitz Roger , Durand ' s nephew , inherited his lands as well as his father ' s office of Constable of England which remained with the lords of Caldicot . Walter ' s son Milo was granted the Earldom of Hereford to add to his titles . De Bohun Family . Milo ' s five sons died childless so his eldest daughter , Margaret , took to her marriage with Humphrey ( III ) de Bohun the Earldom of Hereford , the Constableship of England , and Caldicot . He was responsible for building the stone keep and curtain walls of the present - day Castle . The de Bohun family held Caldicot for over two centuries . Thomas of Woodstock . In 1376 the manor , along with 70 others , passed to Thomas of Woodstock , the third son of King Edward III of England , when he married Alianore de Bohun . On the death of Edward III the throne passed to his grandson , the nine - year - old Richard II . As the new king ' s uncle , Thomas played an important role advising him . He was appointed Constable of England . He rarely visited Caldicot , his main estates being at Pleshey in Essex , close to the seat of power . In 1381 , however , Essex was convulsed by the Peasants ' Revolt . This may be why Thomas decided to spend part of that year in Caldicot . During his stay he gave orders for major new work to be done on the castle . A new gatehouse and drawbridge were constructed . At the rear of the castle a dovecote was replaced by a new tower with private chambers , now known as the Woodstock tower . At the foot of the Woodstock tower two carved stones were to be placed , one marked ' Thomas ' the other ' Alianore ' . As time passed relations between Thomas and King Richard grew increasingly strained . In 1391 , on the orders of the king , Thomas was kidnapped and murdered . His property was confiscated and passed into the hands of the Crown . House of Lancaster . In 1399 Henry Bolingbroke seized the throne from Richard , and although Mary de Bohun did not live to see her husband crowned Henry IV , her son , born at Monmouth Castle , would be one of the country ' s great heroes , Henry V , victor of Agincourt . The division of the de Bohuns estates was revised after the death of Alianore and Mary de Bohun ' s mother Joan , who had outlived both of her daughters by some twenty years . Alianore ' s eldest daughter and heir , Anne , lost Caldicot to Mary ' s son King Henry V , and so Caldicot became part of the great Duchy of Lancaster . Held by Henry ' s widow , Katherine of Valois , Caldicot was later granted into the stewardship of the Herbert family for much of the fifteenth century , and then leased in the sixteenth century to their successors the Somersets with their power base at Raglan . Decline , neglect and restoration . Caldicot Castle was evidently neglected , fell into ruin and became little more than a farmyard . The castle was sold to Charles Lewis of St Pierre in 1857 . In 1885 he sold it to Joseph Richard Cobb , who began the restoration of the castle as his family home . From 1885 to 1964 , the Cobb family owned the castle . Joseph Cobb ' s family remained at the castle after his death and it was his son Geoffrey Wheatley Cobb , and in particular his daughter - in - law Anna , who continued the work of restoration . Geoffrey Wheatley Cobb died in 1931 and after Anna ' s death in 1943 the castle passed to Joseph ' s grandson , Lieutenant Colonel Geoffrey Cobb . In part to counteract the shortage of housing in Caldicot at the time , Geoffrey and his wife Barbara opened the castle to a succession of young married couples and families , who rented furnished apartments in three of the towers and in parts of the gatehouse . In 1964 , Chepstow Rural District Council bought the castle from the Cobb family for £12 , 000 . By then , much council housing was available locally and the tenancies gradually came to an end . The castle , including a small museum , was opened to the public in 1965 . After 1967 , medieval - style banquets were held there . The castle is reputed to be haunted by a number of ghosts and spirits including a grey lady ( who is believed to be Alianore de Bohun ) , hooded monks , a beggar boy and a mischievous poltergeist . At the centre of the activity is the Gatehouse Banqueting Hall ; shadowy figures , as well as moving furniture , have been witnessed in this area . Many people have experienced unusual cold spots , as well as hearing footsteps in vacant parts of the castle . The castle offers Fright Nights and Ghost Tours to visitors wishing to experience these mysterious goings - on for themselves .