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Chepstow, Monmouthshire, perched on its steep hill-side, with its magnificent castle set above the winding Wye, is a glorious point of entry into Wales. Or should one simply say into Monmouthshire? There is a certain amount of border feeling in this delectable part of the country. Before the construction of the great Severn Bridge near by, most motorists entered South Wales through Chepstow, and the steep, winding, narrow streets of the town presented them with a traffic problem that only a bridge could solve. Chepstow, however, rises triumphantly over every problem, even the one of building on its site. The town is set upon the steep western slopes above the River Wye. Immediately to the North, high cliffs begin, which are the glory of this lower reach of the river. Southwards, towards the sea, the marshy banks announce the proximity of the Severn estuary. Chepstow had no option but to climb the hill. The main street twists upwards from the bridge across the Wye, to reach the old town gate, and in between, as the l8th century local poet, the Rev. Edward Davies, proudly declared:
Strange to tell, there cannot here be found
One single inch of horizontal ground.

The name Chepstow is Anglo-Saxon, from ceap (market) and stow (place, town). The Welsh know it as Cas Gwent. The Romans probably forded the river here on their way to Isca Silurum, the modern Caerleon. There are traces of the final sections of Offa's Dyke on the English side of the Wye, North of the town. The Normans recognized the importance of the crossing, and William FitzOsbern. who received the lordship of Hereford from the Conqueror, built the first castle on the site of the present imposing structure. Chepstow was known as Striguil in Norman days. and the Lord of Striguil enjoyed the privileges of the semi-independent Lords Marchers, who guarded the borderland against the Welsh. In the 15th century the Earls of Pembroke added Chepstow to their great estates in Wales. The town developed rapidly in the 14th and 15th centuries and received a charter of incorporation in 1524, although this was suspended in the reign of Charles II through a dispute with the all-powerful Duke of Beaufort. The Urban District Council took over local administration in 1894.

The road bridge over the Wye, now the main entrance to the town, is one of the earliest iron bridges in Britain. It was built by John Rennie in 1816 and underwent extensive repairs in 1968. Chepstow Castle lies to the right of the bridge and is one of the show-pieces of the place. It stands on a spur sloping down from the hill to the westward. The Wye and its cliff made a magnificent defence on the river side, while a deep ditch separated it from the town wall. The site is mentioned in the Domesday Book, and after William FitzOsbern's day the Castle was constantly increased and strengthened, especially by the De Clares in the 12th century, and the Marshalls and Bigods into whose hands it then passed. Under the Earl of Pembroke it became one of the great country houses. The most stirring days of its history occurred during the Civil War. It was held for the King and surrendered in 1645. In the Second Civil War it was surprised by Sir Nicholas Kemeys. who held out in a memorable siege until the Roundheads, under Col. Ewer, broke in and killed Sir Nicholas and routed the garrison. After the Restoration, the Castle was handed back to Lord Herbert. Jeremy Taylor, the Royalist bishop, was a prisoner here. But the most famous prisoner in Chepstow was Henry Marten, the regicide, who spent twenty years incarcerated in the Castle's drum-tower, which now bears his name. Later the Castle fell into decay. It has been carefully restored and is open to the public.

The entrance is through the gatehouse overlooking the town green alongside the Wye. The Marten Tower is the conspicuous round tower you see to your left before you enter. The Castle has four courtyards. The first and largest contains the state apartments, kitchens, and domestic quarters. From the celler below the complex of buildings, the garrison was able to maintain communication with the river, a useful channel of supply during siege. The top storey of the Marten Tower has a small chapel with interesting carvings. Beyond the second court lies the Great Tower, which forms the keep of Chepstow. This is an impressive ruin with thick walls on the river side, where it is separated from the cliff by a narrow pathway. Beyond is a further court, with a gatehouse built in the late 13th century. This defended the western approach to the Castle.

The town walls, known as the Port Walls, began near the top of the Castle ditch, and ran from the Castle in a circuit that brought them down to the riverside about ¾ mile below the bridge. The river formed an adequate defence to the East. The total length of the walls was just under 1 mile, and the defences are still visible for most of the way. A particularly well-preserved stretch starts near the Castle. The town gate stands at the top of High Street and was rebuilt in 1524 by the Earl of Worcester. The battlements and windows are modern. The room over the archway houses the small museum of the Chepstow Society. The bell above the arch was formerly the watch bell of H.M.S. Chepstow.

Bridge Street leads up from the Wye Bridge, and is lined with early l9th century bow-windowed houses. They have surprisingly survived the shaking of the traffic. At the turn at the top of Bridge Street are the Powys almshouses, endowed in 1716. In nearby Upper Church Street are the gabled Montague almshouses, dating from 1613. The parish church, at the top of Church Street, which runs parallel to Bridge Street, has been extensively restored and in parts rebuilt. It is dedicated to St Mary and was originally the church of a Benedictine priory. The tower was rebuilt in 1706; after the alterations of 1841, only the nave and West door remained of the rest of the original structure. The nave is Norman, and the West door is finely decorated with five concentric arches resting on receding columns. The church has preserved some interesting monuments in spite of the drastic restorations. The font is 15th century. The canopied tomb of the 2nd Earl of Worcester and his wife Elizabeth is on the North side of the nave. On the South side of the chancel is the characteristically Jacobean monument of Mrs Clayton, a lady who commemorated her two husbands in the same memorial. On the floor just inside the West door is the gravestone of Henry Marten, inscribed with a verse composed by himself, including the ironic last words of farewell from the old regicide:
My time was spent in serving you and you,
And death's my pay, it seems,
and welcome too.

In the centre of the town lies Beaufort Square, laid out, like everything in Chepstow, on a slope. The medieval stocks from Portskewett were set up in 1947. Nearby is a gun from a captured German submarine presented as a memorial to Chepstow's V.C., William Charles William, the sailor killed at Gallipoli.

Chepstow is now a town of bridges. The Severn Bridge is only a few miles away, but the railway bridge over the Wye represents a fine piece of railway history. It was originally built by Brunel, with a main span of 300 ft. The weight of the span was carried by two enormous tubes, a daring idea at the time. The tubes were removed when the bridge was reconstructed in 1962, but they will be remembered by engineers for the ingenious way in which Brunel harnessed the exceptionally high tides of the Wye to lift the tubes into place. It was Brunel's need to solve the difficult problem of bridging the Wye that led to the establishing of the “Shipyard”, which became the Fairfield constructional engineering works. Fairfield's continued their long tradition of building camions, dock gates, and bridges, when they assembled and launched the deck sections of the Severn Bridge. These floated out to the site in a manner of which Brunel would surely have approved.

Lower down the river from Fairfield's are the Bulwarks, the ramparts of a fine Iron Age fort.

Some 2 miles South West of the town is the little village of Mounton. Between 1727 and 1876 this was a busy place, full of small paper- and corn-mills. Some have delightfully unindustrial names Lark Mill, Lady Mill, Linnet Mill. Mounton was proud to claim that it made the paper for the Bank of England notes. Now the little village is a peaceful beauty-spot, with the gardens of Mounton House perched on the edge of a cliff.

To the North of the town, on the road to Tintern, is the Chepstow racecourse, laid out on one of the finest sites in the country, Piercefield Park. Proud stone lions still guard the entrance gate. Racing men will have a fellow feeling for Valentine Morris, the 18th century grandee, who laid out the park in its present splendour. He was over-generous in his hospitality, and had to leave for the West Indies to restore his fallen fortunes. The tradesmen of Chepstow rang a muffled peal as he drove through the town for the last time.

The park is surrounded by a long stone wall. Once past it, you enter the splendour of the lower valley of the Wye.

Nearby cities: Bristol, Newport

Nearby towns: Berkeley, Caldicot, Lydney, Monmouth, Thornbury,

Nearby villages: Almondsbury, Alveston, Alvington, Aust, Caerwent, Crick, Elberton, Hewelsfield, Hill, Littleton-upon-Sever, Llandenny, Llandogo, Llandogo, Llanfihangel Rogiet, Llangwm, Llanishen, Llansoy, Llanvaches, Llanvair Discoed, Magor, Mathern, New Passage, Newchurch, Oldbury-on-Severn, Olveston, Patchway, Pilning, Portskewett, Raglan, Redwick, Redwick, Saint Arvans, Sheperdine, Shirenewton, St. Briavels, Tidenham, Tintern, Trellech, Undy, Usk, Wolvesnewton, Woolaston

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