1071- Lord William fitz Osbern of Breteuil is created Earl of Hereford a few months after the battle of Hastings by William the Conqueror to subdue the southern Welsh borderlands. He builds the stone keep with materials taken from the nearby Roman town of Caerwent. The town of Cheap-stow -'the market town' is established.
1071 - Earl William fitz Osbern dies in the battle of Cassel in Flanders.
1075 - William's son, Roger, rebels against the king and has his lands forfeited.
1115 - King Henry I grants Chepstow Castle to the de Clare family.
1176 - Earl Richard de Clare - known as Strongbow -dies, leaving a daughter Isabella as heiress to vast estates in Normandy, England, Wales and Ireland. The castle returns to the king.
1189 - King Richard I - 'Lionheart' - marries William Marshal and Isabella de Clare. William Marshal is a loyal knight to Richard's father King Henry II and during a skirmish had unhorsed Richard, but spared his life. William Marshal sets about bringing fitz Osbern's castle up to date.
1219-1245 - William Marshal dies, leaving five sons, all of whom succeed in turn to their father's inheritance and all of whom die childless by 1245, by which time the castle had been much enlarged and strengthened, with walls up to 18 feet thick in places. The death of youngest brother, Anselm, marks the end of his line.
1245 - The Marshal lands are divided amongst their sisters. Chepstow passing to the eldest, Maud, and on her death to her son. Roger Bigod II, earl of Norfolk.
1270 - Death of Roger Bigod II. The castle passes to his son, Roger Bigod III.
1270-1272 - Roger Bigod III strengthens the castle's upper gatehouse in the barbican with a gate tower and portcullis.
1272-1278 -Building of the town wall during an unsettled period of Welsh revolts which saw the beginning of the final conquest of Wales under Edward I.
1278-1285 - Work begins again under the direction of Master Ralf, who is paid a wage of two shillings a week as master mason. The new hall range is built during this period.
1285-1293 - The building of the Marten's Tower at the south-east corner of the bailey to provide extra protection to the main gatehouse. The castle is visited by King Edward I.
1290's - The great tower (William fitz Osbern's original keep) is enlarged and the upper storey added.
1298-1299 - Four large catapults are built and mounted on the four towers by a military engineer. For some reason these were later neglected and three were put into store, where they became useless.
1302 - Partly because of his lavish building works, the childless earl, Roger Bigod who was now approaching old age, makes an agreement with the King that in return for an annuity, his lands and his castles would pass to the Crown on his death.
1306 - Roger Bigod III dies. Chepstow, with its planned building works still unfinished, passes to the Crown. Parts of the castle are described a 'ruinous and unroofed'.
1308-1310 - Building and repair work begins. King Edward grants Chepstow to his half brother, Thomas de Brotherton, but for some years it is in the hands of the king's favourite, Hugh le Despenser.
1326 - King Edward II flees to Chepsow with Hugh le Despenser to try to escape to Ireland. Unfortunately for them the tides were also against them and they are forced to land at Cardiff. They are both later captured. Hugh le Despenser is executed and King Edward faces a gruesome death in Berkeley Castle.
1403 - The castle, which has by now passed to de Brotherton's descendent, Thomas Mowbray, duke of Norfolk, is ordered to be garrisoned against Owain Glyndwr with 20 men at arms and 60 archers. However, the Welsh advance is halted at Usk and so Chepstow sees no action.
1469 - During the Wars of the Roses the castle is again the refuge of fallen royal favourites when Richard Woodville, earl Rivers and his sons, Sir John Woodville, the rivals of Warwick 'the Kingmaker' flee here after their defeat at Edgecote. Warwick pursues them to Chepstow. Upon his arrival the garrison hand the unpopular Woodvilles over to him without a fight. They are later beheaded. At this time the castle has recently been handed over to William Herbert, earl of Pembroke, who is also executed after Edgecote. However, the Herbert's soon recover from this setback and come to dominate the area politically, owning many of its castles.
1500's - During this more peaceable age Chepstow and the new county of Monmouth is controlled by the Somersets, earls of Worcester from their castle at Raglan. Many of the buildings at Chepstow are converted into lodgings for their numerous household.
1643-1645 - At the outbreak of Civil War Henry Earl of Worcester declares Chepstow for King Charles I. In April of that year the parliamentary general William Waller advances on Chepstow but, lacking heavy artillery, he is unable to reduce Chepstow. Other raids and skirmishes follow but it is not until October 1645, with the king's cause rapidly becoming hopeless, does parliamentary artillery finally enforce the surrender of Chepstow's garrison of 64 men and 17 cannon.
1648 - During the outbreak of the second Civil War, the castle is seized by a local Royalist, Sir Nicolas Kemeys. Cromwell, on his way to reduce Pembroke, demands its surrender. When this is refused, he leaves Colonel Ewer and his regiment to reduce it. Ewer's four cannon quickly breach the walls and as his men prepare to storm the castle, many of the garrison surrender. Sir Nicolas Kemeys and the man who original betrayed the castle to him are killed, probably shot out of hand after the castle's fall. The 120 Royalist prisoners were imprisoned in Chepstow church, but later released.
15 Miles East of Newport.
Chepstow Castle is one of the earliest stone castles to be built in England, set high upon a cliff above the River Wye, at the site of a Roman ford, guarding one of the main river crossings from southern England into Wales.
Few castles in Wales are as important than Chepstow in the story of Wales from the period of the Norman conquest. Even today the remains of this important castle are considerable, situated dramatically on the steep cliffs with the red waters of the River Wye winding its way far below. A fabulous castle rich in history and a must see for any castle-finder.