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Chepstow Castle, constructed in 1067 by Norman Lord William FitzOsbern on limestone cliffs overlooking the River Wye in Monmouthshire, stands as the oldest surviving post-Roman stone fortification in Wales and Britain.
William FitzOsbern, a close ally of William the Conqueror, initiates construction of Chepstow Castle in 1067, making it one of the first Norman strongholds in Wales. Positioned on a narrow ridge between a limestone cliff and the Dell valley, the castle secures an essential crossing point on the River Wye, linking Monmouth and Hereford. It suppresses Welsh attacks toward Gloucestershire along the Severn shore.
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Unlike most Norman castles, built as earth and timber motte and bailey structures, Chepstow uses stone from the outset, incorporating recycled blocks from Caerwent Roman town. Named Striguil, meaning “river bend” in Welsh (ystraigl), it serves as the southernmost castle in the Welsh Marches and adopts the name Chepstow from the adjacent market town by the late 14th century.
The Great Tower, completed by 1090, projects strength against Welsh king Rhys ap Tewdwr. No notable settlement exists at the site before the Norman invasion, though it may have been a prehistoric or early medieval stronghold. Gwent’s rulers, who opposed King Harold, may have initially allied with the Normans.
Architectural Evolution
Chepstow Castle’s four baileys, added sequentially, reflect its construction across four major phases, first studied architecturally in 1904, with Perks’ 1955 description long considered canonical, though recent studies refine these phases.
William Marshal, Earl of Pembroke, modernizes the castle in the 1190s, leveraging warfare expertise from France and the Crusades. He builds the main gatehouse, with doors dated by dendrochronology to 1159–1189, strengthens the Middle Bailey with round towers, and possibly rebuilds the Upper Bailey before his death in 1219. His sons—William, Richard, Gilbert, and Walter—expand the Great Tower by 1245.
Roger Bigod, 5th Earl of Norfolk and grandson of Marshal’s daughter Maud, inherits the castle in 1270 and builds a new Lower Bailey range for his family, constructs the Port Wall (1274–1278), adds Marten’s Tower, and remodels the Great Tower.
King Edward I visits in 1284, marking the castle’s role in his Welsh campaign. The castle’s magnificent gates, sheathed in iron with an elaborate lattice framework, are confirmed by dendrochronology as Europe’s oldest surviving castle gates. The castle lacks a strong keep or concentric layout, making it less defensively robust.
Medieval to Tudor Transition (1300–1600s)
From the 14th century, Chepstow’s defensive importance declines, particularly after the England-Wales wars end in the early 15th century. Thomas de Brotherton, Earl of Norfolk, and later his daughter Margaret, control the castle in 1312.
During Owain Glyndŵr’s 1403 rebellion, it is garrisoned with twenty men-at-arms and sixty archers but avoids attack due to its size and limited strategic value, unlike Newport Castle, which is assaulted. William Herbert, Earl of Pembroke, acquires the castle in 1468, and Sir Charles Somerset, Earl of Worcester, remodels it into a grand residence in 1508.
After the Laws in Wales Acts (1535, 1542) incorporate Chepstow into Monmouthshire, it shifts from a fortress to a great house. In the 12th century, it aids the Norman conquest of Gwent, the first independent Welsh kingdom subdued, and is held by powerful magnates William Marshal and Richard de Clare.
English Civil War and Aftermath
During the English Civil War, Chepstow, in Royalist Monmouthshire, faces sieges in 1645 and 1648, falling to Parliamentarians on May 25, 1648. Sir Nicholas Kemeys, who leads the Royalist defense in the Second Civil War, dies in combat after refusing to surrender, with a memorial in the keep. The castle serves as an artillery fort, barracks, and political prison, housing Bishop Jeremy Taylor and Henry Marten, a Charles I death warrant signatory, who dies there in 1680.
Decay and Tourism Boom
The Duke of Beaufort acquires Chepstow in 1682, disbands the garrison in 1685, leading to partial dismantling and neglect, with parts used as a farmyard and glass factory. By the late 18th century, its ruins become a “charming” feature on the Wye tour from Ross-on-Wye. Charles Heath publishes the first guidebook for the castle and town in 1793. J.M.W.
Turner paints the castle in 1794, with the artwork sold to Chepstow Museum in 2023. Tourism grows by the 1840s with steam ship day trips from Bristol, and the castle hosts horticultural shows, fêtes, and historical pageants from the 1880s, sanctioned by the Duke of Beaufort, who fails to sell it in 1899.
20th Century and Modern Era
Dr. Orville Ward Owen excavates the castle and riverbed in 1910–1911, seeking Francis Bacon’s documents to prove he wrote Shakespeare’s plays. The 1913 film “Ivanhoe,” starring King Baggot, is shot on the grounds. William Royse Lysaght purchases and conserves the castle in 1914, and the Lysaght family transfers it to the Ministry of Works in 1953. It serves as a filming location for Terry Gilliam’s “Jabberwocky” (1977), HTV’s “Robin of Sherwood” (1984–1986), Sepultura’s “Chaos A.D.” (1993), and Doctor Who’s 50th anniversary broadcast. Since 1984, Cadw manages the Grade I listed castle, allowing public access to battlements and Marten’s Tower, with frequent special events.
Other Ancient Welsh Castles
Twthill Castle (1073)
Robert of Rhuddlan, under William the Conqueror’s command, builds Twthill Castle in 1073, overlooking the River Clwyd as a Norman headquarters for North Wales. It may have been the site of Welsh Prince Gruffud ap Llewelyn’s royal palace, suggesting an older motte. By 1086, it has a church and mint, but falls into disuse after the stone-built Rhuddlan Castle replaces it. For 200 years, it serves as a hub for merchants and craftsmen.
Camrose Castle (1080)
Camrose Castle, constructed in 1080 as a Norman motte and bailey over Camrose Brook, hosts William the Conqueror during his pilgrimage to St David’s. Later rebuilt with a stone wall, it remains a partially overgrown classic motte and bailey.
Cardiff Castle (1081)
Cardiff Castle, built in 1081 within a Roman fort’s walls as a Norman motte and bailey, withstands Owain Glyndŵr’s 1404 attacks. Rebuilt multiple times, including by the 3rd Marquis of Bute, it serves as an air raid shelter during World War II with tunnels for thousands. Its modern rendition appears on Welsh Castle Coasters.
Caerleon Castle (1085)
Caerleon Castle, a 1085 Norman motte and bailey near a Roman fortress and baths, is captured by the Welsh in 1217, rebuilt in stone by William Marshal, and ruined during Owain Glyndŵr’s 1402 revolt. Its tower ruins stand near the Hanbury Arms, linked to myths of King Arthur’s palace.
Caldicot Castle (1086)
Caldicot Castle, recognized by Normans in 1086, features a timber motte and bailey overlooking the Severn estuary, with a green motte and a round stone keep built around 1221. It offers views of the River Nedern and 55 acres of parkland, remaining a well-preserved hidden gem.
Abergavenny Castle (1087)
Abergavenny Castle, a 1087 motte and bailey, hosts the 1175 Massacre of Abergavenny, where William de Braose kills unarmed Welsh lords, including Sytsylt ap Dyferwald, in the great hall. Its square keep, built in 1819, now houses Abergavenny Museum.
Castell Aberlleiniog (1090)
Hugh d’Avranche, 1st Earl of Chester, builds Castell Aberlleiniog in 1090 on a sloping hill in Anglesey, the only motte and bailey there. It survives a 1094 siege by Gruffydd ap Cynan, who later drives out Hugh, keeping Anglesey under Welsh control until King Edward I’s arrival. The visible stone castle dates to the mid-17th century English Civil War defenses.
Pembroke Castle (1093)
Roger of Montgomery constructs Pembroke Castle in 1093 as a motte and bailey during the Norman invasion, never falling to the Welsh. William Marshal rebuilds it in stone in 1189, featuring a cylindrical tower with a stone dome, depicted on Welsh Castle Coasters. A cave below shows 12,000 years of occupation.
Castell Carn Fadryn (300 BCE, Medieval 1188)
Castell Carn Fadryn, on the Llŷn peninsula, begins as an Iron Age hillfort in 300 BCE, reinforced in 100 BCE, and sees a medieval stone castle built in 1188 by a son of Owain Gwynedd within the hillfort’s remains. Built to assert power among the Sons of Gwynedd, not against the English, it offers views of Anglesey, Cardigan Bay, Snowdonia, and Ireland’s Wicklow Mountains.
Conclusion
Chepstow Castle, erected in 1067, remains Wales’ and Britain’s oldest surviving stone castle, its iron-sheathed gates and limestone perch narrating a 958-year saga of Norman conquest, medieval power, and modern tourism. From Twthill’s Norman hub to Cardiff’s wartime shelter and Castell Carn Fadryn’s ancient hillfort, Wales’ ancient castles, as the “Land of Castles,” preserve a rich tapestry of history for visitors today.
