In the Middle Ages much of the coastal strip was marshland which could only be crossed by fords. In past centuries much of Flintshire was covered by thick forest apart from the peaks of the Clwydian Hills and other highlands. The earliest inhabitants lived on the highlands above tree-line. As the population increased and people learnt more about the art of agriculture and had better tools they made clearings in the forest and built villages in the valleys and along the coast.
Although William became King of England in 1066, Chester was still held in 1070 by Edwin, Earl of Mercia. However William crossed the Pennines from Yorkshire and caught Edwin by surprise and after a brief struggle Edwin surrendered. This was the end of any serious Saxon hope of driving out the Normans and returning the kingdom to Saxon rule. Earl Edwin died in 1071 attempting to flee to Scotland, at the hands of his own followers. The walls of Chester were re-built and a castle constructed on the banks of the River Dee. William also had built castle outposts at Shotwick, Hawarden, Pulford and Holt. His nephew Hugh became Earl of Chester and quickly extended his lands into Wales where he built a castle at Rhuddlan in 1073. Flintshire had been included in the Earldom of Chester. (Henry III annexed the Earldom to the crown and made his son, later Edward I, Earl of Chester and Flint in 1241. Until 1727 all Prince's of Wales were created Earl of Chester and Flint). By 1080 the Normans controlled all the coastlands between the Clwyd and the Conway and built another castle at Deganwy. The Welsh did not know how to attack castles or how to fight against knights on horseback and it took some years for them to adapt to the new way of fighting.
William the Conqueror, though he seems to have had no intentions of invading Wales, wanted to ensure the stability of the frontier. Rather than trying to hold the border himself, he gave lands along the Welsh hinterland to his strongest and most loyal supporters. Roger Montgomery received Shrewsbury, William Fitzosbern got Hereford, and Hugh of Avranches (Hugh the Fat) was given Chester. These barons encouraged their followers to push gradually westward into Welsh territory. The Normans possessed several "weapons" which gave them an advantage over the Welsh. The Norman knights were better armoured and horsed than the Welsh, and they erected castles to hold each parcel of territory they carved from Welsh holdings.
The early Norman castles were simple motte and bailey affairs; basically an earthen mound surrounded by a wooden palisade. These wooden castles were gradually replaced by more massive - and more easily defended - castles of stone.
William Fitzosbern overran the kingdom of Gwent, but he had no time to enjoy his triumph. He died in 1071 and when his son was imprisoned for treason in 1075 the Earldom of Hereford was abandonned. Although this initially gave the Welsh in the south-east a breathing space, their relief was not to last long. A number of Norman landowners established small fiefdoms along the border. William visited Wales in 1081, making a pilgrimage to the shrine of St. David, a visit that allowed him to display his wealth and power to the Welsh. Although William acknowledged Rhys of Deheubarth as ruler of that kingdom, Rhys wisely agreed to pay Willliam an annual tribute. Grufudd ap Cynan was not so lucky - he was captured by Hugh the Fat of Chester and kept in prison for 12 years. Hugh's cousin Robert took much of Grufudd's lands, and the Normans seem to have regarded Gwynedd as a part of their kingdom. But the threat to Welsh territory did not stop at Gwynedd. Roger, Earl of Shrewsbury pushed deep into Powys. Around 1086 he built a castle at the ford of Rhydwhiman across the Severn, and named the place Montgomery. In 1087 William the Conqueror died, to be replaced on the English throne by his second son, also named William. The second William was not the forceful ruler his father had been, and he did nothing to restrict the ambitions of the Normans in Wales.
As we all know, William ordered his men to collect information about his new kingdom and this information has become known as the Domesday Book (also known as Doomsday Book). As Flintshire was regarded as part of the English kingdom it was included in the survey. In 1086 there were 226 houses in Chester. The most important part of Flintshire was Rhuddlan where there was a castle and church, a mint, corn mills and fisheries with 18 burgesses with numerous serfs and villeins. Other parts of Flintshire mentioned are Atiscros and Northop and Maelor Saesneg. Atiscros was the land around Oakenholt. The manor of Northop was then held by Hugh, the earl of Chester. There were 346 families recorded in Flintshire in the Domesday Book with a total of 2000 people. There were churches at Halkyn, Llanasa, Gwespyr, Meliden, Dyserth, Rhuddlan and Gwaenysgor.
Earl Hugh died in 1099 and was succeeded by his 7 year old son and the Prince of Gwynedd, Gruffydd ap Cynan (1081-1137), was able to retake the disputed lands. From 1100 to 1114 the prince, Gruffydd ruled over the whole of Flintshire. Then the Earl became 21 and wanted his lands back. Combined with the Kings of England and Scotland he invaded Wales and Gruffydd surrendered the disputed lands up to the River Clwyd to the Normans. Gruffydd died in 1137 and was succeeded by his son Owain ap Gruffydd who reigned 1137-70. At that time the English were in Civil War with Matilda fighting Stephen for the throne and Owain used the confusion to retake Flintshire from the Normans. There was a battle at Coleshill in 1150 where Owain defeated an English army led by the Earl of Chester assisted by the Prince of Powys, Madog ap Maredudd. It was not until 1157 that King Henry 11 invaded Wales to put an end to the independence of the Welsh princes.
The main English army crossed the Saltney marshes and moved along the coast towards Basingwerk but Owain was aware of the situation and when a small party including King Henry broke away he caught them unprepared in Ewloe woods and beat them. There was a second battle at Coleshill where Owain was again successful but was repulsed. Owain had to retreat in view of the large numbers of troops against him and peace was arranged with the disputed lands returning to English control. The fields south of Bagillt are known as 'Hill of Retreat'. In 1163 Henry quarrelled with Thomas Becket, Archbishop of Canterbury and during the dispute the Welsh again attempted to win control of Flintshire and in 1166 were successful. Owain died in 1170 and was succeeded by Dafydd who made peace with Henry even marrying his half-sister but he paid homage and acknowledged Henry as his overlord. This peaceful period ended in 1194 when Llewelyn ap Iorwerth, (the Great) the son of Dafydd's brother decided to become Prince of Gwynedd and by 1198 he had succeeded. In 1199 he captured Mold Castle from the English. In 1199 he made peace with King John, again acknowledging him as his overlord, and in 1205 marrying his daughter. However King John was greedy and in 1210 he invaded Wales and forced Llewelyn to make peace and all lands east of the Conway returned to English control. In 1213 King John was in dispute with his barons and Llewelyn took advantage of the situation and made peace with John and later the Earl of Chester whereby the lands returned to Welsh control. He was a powerful force on the side of the barons in their struggle with King John, and three clauses of Magna Carta (1215) declare his privileges and recognize the independence of the law administered by him. Though he did homage (1218) to John's successor, Henry III, Llewelyn continued fighting against the English until 1234. Llewelyn was shrewd enough to realize that England was ultimately invincible, and at the end of his life he tried to secure for Wales the continuation of peace by placing the country in feudal dependence on the king of England, by a treaty made through the bishops of Chester and Hereford. By this treaty Llewelyn gave away the semblance of Welsh independence while retaining the reality of it, but this involved the succession of Dafydd, his son by an English mother and the cousin of the king, and the disinheriting of Griffith, born of a Welsh mother. Griffith was able and forceful, whereas Dafydd was not, and the sympathies of many in Wales were with Griffith and with his policy of hostile independence of England. Llewelyn could not reconcile his sons, and retired to the Cistercian monastery at Aberconwy, where he died in 1240. Llewelyn died in 1240 and was succeeded by his son Daffydd (David) who died in 1246 and was eventually succeeded by his nephew Llewelyn ap Gruffudd (the Last) who was prince until he was killed in 1282. He was succeeded by his brother, Daffydd who was killed in 1283.
Prior to the Norman Conquest the district was in the hands of Edwin, the last Earl of Mercia (c1026-1071). He was killed by his own men when he tried to escape from King William to Scotland. Near to Bryn Edwin in Flint Mountain are the foundations of an ancient site called Llys Edwin where he lived. This was just one of his many homes as he was a very wealthy man. He was the grandson of Lady Godiva (of Coventry fame), and was the brother-in-law of King Harold (Godwinson).