Chepstow is a town and community in Monmouthshire, Wales, adjoining the border with Gloucestershire, England.
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Chepstow Castle, situated on a clifftop above the Wye and its bridge, is often cited as the oldest surviving stone castle in Britain.
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The port of Chepstow became noted in the Middle Ages for its imports of wine, and became a major centre for the export of timber and bark, from nearby woodland in the Wye Valley and Forest of Dean.
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Chepstow is well known for its racecourse, which has hosted the Welsh National each year since 1949.
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Chepstow is on the western bank of the Wye, while adjoining villages on the eastern bank of the river, Tutshill and Sedbury, are in England.
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The name Gwent itself derives from the Roman settlement Venta Silurum or 'Market of the Silures', now named Caerwent, 5 miles west of Chepstow, which had been the Romano-British commercial centre of south-east Wales.
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Oldest site of known habitation at Chepstow is at Thornwell, overlooking the estuaries of the Wye and Severn close to the modern M48 motorway junction, where archaeological investigations in advance of recent housing development revealed continuous human occupation from the Mesolithic period of around 5000 BC until the end of the Roman period, about 400 AD.
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Chepstow is located at a crossing point directly between the Roman towns at Gloucester and Caerwent (Venta Silurum).
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The Lancaut and Beachley peninsulas, opposite Chepstow, were in Welsh rather than Mercian control at that time, although by the time of the Domesday Book Striguil was assessed as part of Gloucestershire.
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Chepstow Castle was founded by William fitzOsbern, 1st Earl of Hereford, in 1067, and its Great Tower, often cited as the oldest surviving stone fortification in Britain, dates from that time or shortly afterwards.
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Chepstow was given its first charter in 1524, and became part of Monmouthshire when the county was formed.
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Chepstow reached the peak of its importance during the Napoleonic Wars, when its exports of timber, for ships, and bark, for leather tanning, were especially vital.
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An important aspect of Chepstow's trade was entrepot trade: bringing larger cargoes into the manageable deep water of the Wye on high tide and breaking down the load for on-shipment in the many trows up the Wye to Hereford past the coin stamping mill at Redbrook, or up the Severn to Gloucester and beyond.
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Chepstow traded across the estuary to Bristol on suitable tides to work vessels up and down the Avon to that city's centre.
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The historic centre of Chepstow occupies part of a bend in the River Wye, and slopes up from the river to the town centre and beyond.
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Bedrock of Chepstow is limestone, mudstone and sandstone, overlain in places with some gravels and the clay and silt of the river's tidal flats, which are of marine origin and up to two million years old.
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The rock of Sedbury cliffs and those under Chepstow Castle are Carboniferous Limestone, hundreds of metres thick in the area, made of particles and shells of sea creatures from 330 to 360 million years ago.
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Layered outcrops of darker Black Rock Limestone, which makes up a broad part of Chepstow's bedrock, are very clear in cliffs along Craig yr Afon, part of the Wales Coast Path extending from Wyebank Road, and by the link road from Bulwark Road to the M48, where the looser reddish Mercia Mudstone and the lighter Hunts Bay limestone are seen.
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Chepstow is administered by Monmouthshire County Council, one of the 22 unitary local authorities in Wales formed in 1996.
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Chepstow was an electoral ward to Gwent County Council between 1973 and 1996.
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Until January 2020 Chepstow was within the Wales constituency for the European Parliament.
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Chepstow developed from mediaeval times as a port and trading centre.
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In 2018 Chepstow was declared by campaign group Surfers Against Sewage to be the first "Plastic Free Town" in south Wales.
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Chepstow is located close to junction 2 of the M48 motorway, at the western end of the Severn Bridge.
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Chepstow is serviced by Transport for Wales Rail; the service provided by CrossCountry from Cardiff Central to Nottingham, via Birmingham New Street.
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The line at Chepstow was blocked by a landslide on 12 November 2009, following heavy rain.
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Town is served by Chepstow School, located on Welsh Street, with over 1, 300 pupils.
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Tutshill and Sedbury, on the English side of the Wye but within walking distance of Chepstow and attracting some pupils from the town, have their own schools, including Wyedean School, and the private preparatory Dean Close St John's in Tutshill.
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Chepstow has no cinema or theatre, although film showings, theatrical and other events regularly take place in the Drill Hall, close to the Castle and riverside area.
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Chepstow Racecourse is the leading horse racing facility and course in Wales.
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Chepstow RFC was founded in 1878, by pupils and staff of Chepstow Grammar School.
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Chepstow has held professional and amateur street cycling events, such as the Chepstow Grand Prix.
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Chepstow Harriers running club, founded in the 1880s, meets twice weekly at the centre in addition to scheduled events.
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Chepstow contains five Grade I listed buildings – the Castle, Priory Church, Town Gate, Port Wall and Old Wye Bridge – and several with Grade II* listed status.
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Chepstow Priory was established in 1067, at the same time as the castle.
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The riverside area of Chepstow was once an open area of shipyards surrounded by warehouses.
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Able Seaman William Charles Williams, who was born in Shropshire but raised in Chepstow, was posthumously awarded the Victoria Cross for gallantry in World War I A gun from a captured German U-boat was presented to the town to mark his bravery, and stands in the town's main square beside the War Memorial.
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