Stronghold in the Marches

Chepstow is an historic fortress town in Monmouthshire, Wales. Set on the Wye River near the border with Gloucestershire, it features an imposing Norman castle that’s built on a spur and looks down on the town’s steep medieval streets.


Local archaeological excavations in the Thornwell area of Chepstow suggest continuous human occupation from about 5000BC to around 400AD. Iron Age fortified camps to the north and south of the town centre lend credence to these findings, as does Chepstow’s position at a crossing point between the Roman towns of Caerwent and Gloucester. For some historians, the discovery of Roman artefacts also indicates the existence of a Roman camp although firm evidence has yet to be uncovered.

Kingdom of Gwent

After the Romans left, Chepstow became part of the Kingdom of Gwent – a medieval Welsh dominion that lay between the Rivers Wye and Usk. Drawing on the culture of the war-like Silures tribe, which actually pre-dated the Romans, this successor state remained in existence right up until the Norman Conquest. And it is the Normans who are considered the proper founders of modern Chepstow.

Norman Occupation

Following the Norman Conquest Chepstow once again became an important strategic location. Its low bridging point on the River Wye provided the ideal location from which to launch expeditions into rebellious Wales, while controlling river access to Hereford and the Marches.

Chepstow Castle Walls

So within months of William the Conqueror being crowned King of England, loyal Norman lord William FitzOsbern was tasked with building a fortress.

Construction of Chepstow Castle began in 1067 with its Great Tower completed by around 1090. A Benedictine priory, which is now St Mary’s Church, was also founded nearby.

Made from locally-quarried stone, the castle’s precipitous location atop limestone cliffs helped to establish Chepstow as a Norman stronghold.

Reputation as Port

Operating under the Marcher Lordship of Striguil, Chepstow became a key port exporting timber and bark cut from the Wye Valley and Forest of Dean. Large quantities of wine were also imported from Gascony, Spain and Portugal.

Bigod’s Building Project

In 1270, Roger Bigod, the 5th Earl of Norfolk, gained control of the lordship and soon embarked on an ambitious building project that would eventually transform Chepstow. The castle was expanded and an enormous defensive tower constructed (Marten’s Tower). Even Tintern Abbey was rebuilt. This was followed by the building of the Port Wall and Town Gate in around 1274.

Role as Market Town

Some twenty years later, Bigod granted his associate John ap Adam the right to hold a market in Chepstow. The wall and town gate helped ensure that access to the market was only granted to those who agreed to pay tolls. Bigod was also responsible for the creation of an annual fair.

Despite the occasional incursions by the Welsh, the castle’s importance gradually diminished. Nevertheless, Chepstow continued to thrive during the medieval period, becoming one of the largest ports in Wales. This was partly helped by the fact that the town, which still operated under a Marcher Lord, was exempt from Crown-imposed taxes.

It was around the 13th century that the name Chepstow was first recorded. It derives from the old English terms ‘ceap or chepe stowe’ which means ‘market place’ or ‘trading centre’.

15th Century – Charter, Civil War

In 1524 Chepstow gained a charter and was integrated into the historic Welsh county of Monmouthshire. Although the town continued to flourish, the castle once again became a strategic military target, this time because of the English Civil War. Despite being initially held by Royalists, the fortress was besieged by Parliamentary forces from neighbouring Gloucestershire in 1645 and again in 1648, before eventually falling in May of 1648.

Largest Port in Wales

Following the tumult of the civil war, Chepstow’s port remained prosperous. By the 1790s it was handling a greater tonnage of cargo than Cardiff, Swansea and Newport combined. Its export of timber, bark and leather tanning became particularly important at the turn of the century, when the Napoleonic Wars broke out across continental Europe.

Entrepôt trade also played a major role in Chepstow’s economy during this period. Large imported cargoes would be ferried to the deep waters of the River Wye during high tide. These would then be broken down and loaded onto smaller trows for shipment up the River to places like Hereford and Gloucester.

Wye Valley Landscape

Observations on the River Wye

It was during the late 18th century that tourism first took hold in Chepstow thanks largely to the Wye Tour – a boating excursion popularised by the publication of artist William Gilpin’s Observations on the River Wye.

In the book he described the Wye Valley as an area rich in picturesque landscapes. Because of this account and due to the fact that the Napoleonic Wars prevented British travellers from touring Europe, visitors flocked to the area.

Ross-on-Wye and Monmouth served as launching points with boats ferrying tourists down river to Chepstow, the tour’s final destination. During the excursion, these early tourists would paint and draw local landscapes as well as major landmarks such as Tintern Abbey and Chepstow Castle.

19th Ship Building, Decline

Alongside tourism, shipbuilding, rope-making and even the production of clocks remained important industries for Chepstow in the 19th century. Sadly though, trade eventually started to decline as Cardiff, Newport and Swansea became the preferred options for handling coal and steel from the South Wales valleys.

Role as Wartime Shipyard

However, shipbuilding enjoyed a revival of sorts during the First World War with the opening of National Shipyard No.1. Eight slipways were laid down for the mass-production of ships for the war effort although part of Chepstow’s 13th century wall also had to make way.

Some twenty thousand workers were brought in to meet the demand, which lead to the creation of residential areas such as Hardwick and Bulwark.

Severn Bridge, Chepstow

Severn Bridge Opens

The opening of the Severn Bridge in 1966 helped Chepstow’s development considerably. Previously, the only way to commute to Bristol and other major towns such as Cardiff was by ferry. But the new bridge ushered in a new period of prosperity.

Redevelopment of Town Centre

The town centre underwent a major £2 million redevelopment in 2004-5 which included the addition of various sculptures and public art. Although not to everybody’s taste, the scheme received numerous national awards. The riverside has also been landscaped in recent years to help guard against flooding.

Modern Chepstow

Today, Chepstow is a vibrant market town that retains much of its fascinating heritage. Despite the ebb and flow of history, strong medieval influences can still be seen in the narrow cobbled streets and the Grade II-listed townhouses at Beaufort Square. Many Georgian dwellings remain intact as too, such as the terraced properties on Castle Terrace.

Good shopping is to be had in Chepstow. Among the stately Georgian and Victorian buildings is an assortment of independent boutiques and outlets. Some of the best can be found on the pedestrianised St Mary’s Street which features bookshops, antique stores, cafes and top restaurants. Read on as we now take a closer look at some of the most notable Chepstow visitor attractions.

Chepstow Castle, Monmouthshire

Chepstow Castle

Chepstow Castle is the town’s most recognisable landmark. This wonderfully preserved castle is set on limestone cliffs overlooking the River Wye and affords some outstanding views of the Wye Valley and beyond.

Despite being modified over the years to withstand ever more destructive weaponry, the castle remains a typical example of a Norman keep.

It comprises a large gatehouse and a series of towers connected by high curtain walls. The battlements are accessible to visitors as is the impressive Great Hall. Other highlights include the iron-plated castle doors that are on display inside the castle.

Originally thought to date from the 13th century, forensic analysis has revealed them to be much older – it is thought they were constructed some time before the 1190s. A set of replica doors now stand in the gatehouse. See the link below this article for further information about visitor times and admission prices.

The Port Wall

Chepstow’s famous ramparts are another historical highlight. They originally comprised a 13ft high stone curtain wall that stretched from the south side of Castle Dell some 700 metres to the bank of the River Wye.

This was punctuated by ten semi-circular towers. Although partly breached to accommodate a railway line and shipyard, large sections remain intact including the Port Wall, Town Gate as well as some of the towers.

The best places to view the walls are near the railway station and on the east side of town, just off of Welsh Street. Some of the more well-preserved sections, which include a semi-circular tower, are to be found west of Chepstow’s library.

Chepstow Museum

Chepstow Museum is located opposite the castle and occupies an impressive Georgian townhouse. It offers fascinating insights into the long and varied history of this ancient town through a large collection of photographs and posters.

These showcase the many industries that aided in Chepstow’s development including the wine and timber trades, shipbuilding and salmon fishing. The museum also houses an impressive collection of 18th and 19th century prints which illustrate the beauty of the Wye Valley and local area. Admission is free and there’s also a well-stocked shop.

St Mary’s Church

The centrally-located St Mary’s Church is a Grade I listed building and a major local historical site. Founded as a Benedictine priory in the late 11th century by William FitzOsbern it features an ornate West doorway which dates from this very period. The church also houses an organ with pipe-work from the 17th century.

Tintern Abbey, Monmouthshire

Tintern Abbey

The Gothic Tintern Abbey is another major visitor attraction near Chepstow that’s set on the west bank of the River Wye. The site comprises an imposing, roofless cruciform church and a collection of monastic buildings.

Founded by Cistercian monks in the 1132, it is one of the finest ecclesiastical ruins in the UK.

Following the Dissolution of the Monasteries, this majestic building fell into disrepair and lay derelict for hundreds of years. But it was eventually immortalised by the likes of William Gilpin and later, William Wordsworth in his collection of poems, Lyrical Ballads. In 2000, the abbey was assigned Grade I listed status.

Old Wye Bridge

Old Wye Bridge was opened in 1816 and is the largest iron arch bridge in the world. It was designed and built by famed engineer, John Urpeth Rastrick who also built steam locomotives. Situated near Chepstow Castle, the structure is a monument to the ingenious engineering work of the industrial revolution.

As testament to this Regency-era ingenuity, the bridge has stood the test of time and remains in use to this day. Listed as a Grade I building in 1975, there have also been calls for it to be granted World Heritage Site status such is its historical importance.

Severn Bridge

The Severn Bridge is also an important structure in its own right. This cherished suspension bridge spans both the River Severn and River Wye, connecting Chepstow and Aust in South Gloucestershire. Opened in 1966 by Queen Elizabeth II, the bridge helped ease traffic congestion and became an important crossing point between England and Wales for many years.

It actually comprises four separate components: Aust Viaduct, Severn Bridge, Beachley Viaduct and Wye Bridge. In 1998, the latter received Grade II status. The suspension towers stand at 445 ft while the bridge itself is more than 5000 ft in length.

One of the best places from which to view the Servern Bridge in all its splendour is via an observation deck at the Severn View Services Station on the Gloucestershire side.

Lancaut Nature Reserve

Lancuat Nature Reserve is about 3 miles north of Chepstow and is home to an abundant array of plant species and birds. Its cliffs form an ideal habitat for peregrine falcon and raven while the River Wye, which flows lazily through its confines, attracts heron and Cormorant.

The reserve offers some wonderful woodland walks that take in historical landmarks such as the ruined St James Church – a Grade II listed chapel. Some of the best riverside views can be found at Wintour’s Leap – a popular rock climbing location and viewpoint that’s located on the English side near the village of Woodcroft.

Offa’s Dyke Path

The 8th century Offa’s Dyke Path provides an additional opportunity to appreciate the picturesque border countryside. The 177 mile path wends its way from Chepstow to Prestatyn, across an unspoilt landscape that comprises the Brecon Beacons National Park, the AONB-designated Shropshire Hills and the stunning Dee Valley – also an Area of Outstanding Natural Beauty.

Other highlights include the beautiful Hay-on-Wye, Pontcysyllte Aqueduct and the ruined Augustinian priory at Llanthony.

Learn more about Chepstow via the official Visit Monmouthshire website.

Looking to stay in the Wye Valley? Then take a look at our featured self catering properties in the region.

Dale Shelabarger

Dale is the owner and founder of Cottages to Rent which he launched back in 2005. As well as promoting holiday cottages, Dale blogs regularly about top UK holiday destinations, visitor attractions and places of historical interest.