Chepstow is significant for its size, unsullied ruins, and historical significance. When the Normans arrived in 1066, William immediately began building castles to defend his new domains. Many started as motte and bailey fortresses with stone being added later. William's new Marcher lords were no less enthusiastic to shore up their power. The newly minted Earl of Herefordshire, William Fitz Osbern, immediately began buildling castles across his domains. As both a cousin and childhood friend of the Conqueror, Fitz Osbern was a man of great ambition, ferocity, and energy. He began at least a half dozen castles and fortified towns of the earldom. including nearby Berkeley and Monmouth.
The site for Chepstow was selected because it guarded a crossing across the River Wye (now the English-Welsh border). The castle was listed as Striguil (a bend ) in the Doomsday Book, a nod to its location on the Wye. It is likely the oldest non-Roman stone structure in the Isles. Several towers are remarkably intact, but the only complete structure from Fitz Osbern's efforts is the Great Tower that loops between the Middle and Upper Baileys.
The castle complex towers over the River Wye below with the northwest edge making use of the river cliffs for added protection. Its strategic position allowed it to guard the lucrative boat routes on the Wye that carried goods down the river. The Wye is tidal here (thanks to the meeting of the Severn) and depending on time of tide, the water can come up to the castle or be several meters below.
After Fitz Osbern's death on the battlefield in Flanders, his son, Roger, inherited the title and his father's many castle projects. The new earl butted heads with William. Defying the king, he married his sister, Emma, to the Earl of Norfolk. This noncompliance resulted in the Revolts of Earls. William came out with the upper hand and Roger was tried for treason and forfeited his lands. Only William's death brought him reprieve.
The Castle then went to the mighty de Clare family who held it for most of the 12th century. Few changes were made at Chepstow, but they did continue to invest in the surrounding area including the founding of Tintern Abbey in 1131. The de Clare heiress, Isabella, wed the legendary William the Marshal. Despite the political machinations around the marriage and the difference of ages, their marriage seemed to be a happy one. Except for a lengthy stay in Isabel's Irish holdings, the couple were regularly at Chepstow and embarked on improvements to the complex. Marshal drew on his knowledge from the Crusades to incorporate the latest defensive technology in his plans. The great gatehouse at Chepstow is thought to be the first twin towered gate in Britain. The rounded shapes eliminated blind spots for defenders, deflected weaponry better than flat walls, and protected the castle against undermining. Remarkably, the original gate doors survive from Marshal's building program. Dating to the 1190's, they are the oldest doors in Europe. They no longer hang at the gate - they were moved inside the caslte in the 1960s to protect them from weather after almost 800 years at their post.
William and Isabel's five sons inherited the title and castle in succession, but no male heirs remained. The castle then shifted to William's oldest daughter, Maud, and her husband, Roger Bigod, Duke of Norfolk. Their son initiated the next great building phase at Chepstow. Bigod added an extensive range of buildings in the Lower Bailey. What we see today is largely his work. His renovations included a kitchen, serving passages, a new hall, and Marten's tower, likely to house important guests.
The tower in the middle bailey was converted to a kitchen during the Tudor period under the supervision of Earl of Somerset. Like many of the ground floor rooms, it does not have an internal access to upper floors. This was for protection if the walls were breached. Wooden exterior stairs or the wall walk would have provided access between the buildings.
The Great Tower was accessible through the great westward facing door on the western side. The ground floor served as a cellar and storeroom while the upper space was divided into two floor. The windows overlooking the Wye were added at a later date - originally this wall was solid for defense. Note the painted plaster recreation in one of the semi-circular niches. This gives you an idea of how the hall might have been decorated. Great magnates were itinerant moving between all of their castles. Each move, paintings and furniture were loaded onto carts and brought to the next destination. These items were far too precious during the medieval period to have a collection at each home.
Entering the Upper Bailey, accessed through a gallery along the Great Tower, there is a semi-demolished tower. This was the farthest reach of the castle until the Upper Barbican was added. During the Marshal's time, this would have served as his family's private lodgings. the wall here was lowered and widened to support canons during the 17th century.
The Upper Barbican was a later addition. The rock cut ditch that guests walk over was the original edge of the complex. The barbican features an open rounded tower that allowed defenders to protect the weaker side of the castle from a wide angle. To the west, there is another gate featuring standard technology with portcullis, drawbridge, and arrow loops.
Chepstow is managed by Cadw. For current hours check here. An audioguide is included with admission. The castle has decent signage as well as kids' activities throughout. The grounds are somewhat accessbile, but it certain places, ramps are quite steep. A portable induction loop is available, too. Sensory concerns are a minimum.
There is pay and display parking at Castle Dell Car Park. Current rates here. You can pay by exact change or by using the PaybyPhone app. EV parking and bike storage is as available. There are four disabled spaces and the path up to the castle is sloped. Note that restrooms for the site are those in the car park so stop first, especially if exploring with young children. If it is full, the Nelson Street Car Park is nearby and well positioned to explore the village before or after your visit.
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