Chepstow Town Gate

The Port Wall in Chepstow, Monmouthshire, Wales, is a late thirteenth century stone wall, which was constructed for the twin purposes of defence and tax collection by permitting users of the town's market only one point of access through the wall at the Town Gate. The wall originally formed a semi-circle extending for some 1,100 metres (3,600 ft), roughly southwards from Chepstow Castle to the River Wye. It enclosed an area of 53 hectares (130 acres), including the entire town and port as it existed at that time. Substantial sections of the wall remain intact, and both the Port Wall and the Town Gate are Grade I listed buildings. The Port Wall is a Scheduled monument.

14 Beaufort Square in Chepstow, Monmouthshire, Wales, is a townhouse of medieval origins. The present building was mainly constructed in the early 19th century. It is a Grade II* listed building.

Chepstow War Memorial, in Beaufort Square, Chepstow, Wales, commemorates the men of the town who died in the First and Second World Wars. It was designed by Eric Francis, a locally-born architect. The memorial's Neoclassical design is uncommon. The memorial site also includes a German Naval deck gun, donated to the town by George V in commemoration of the posthumous award of a Victoria Cross to Able Seaman William Charles Williams, who grew up in Chepstow and was killed at Gallipoli. Chepstow War Memorial was designated a Grade II listed structure in 1975.

Raglan Lodge is a Grade II* listed building in Beaufort Square, Chepstow, Monmouthshire, Wales. Though the frontage dates from the early 19th century, parts of the building date from the medieval period and the ground floor vaulted hall was probably the town's 14th century moot hall. The building has been refurbished and is currently used as a backpackers' hostel.

Chepstow (Welsh: Cas-gwent) is a town and community in Monmouthshire, Wales, adjoining the border with Gloucestershire, England. It is located on the tidal River Wye, about 2 miles (3 km) above its confluence with the River Severn, and adjoining the western end of the Severn Bridge. It is the easternmost settlement in Wales, situated 16 miles (26 km) east of Newport, 28 miles (45 km) east-northeast of Cardiff, 18 miles (29 km) northwest of Bristol and 110 miles (180 km) west of London. Chepstow Castle, situated on a clifftop above the Wye and its bridge, is often cited as the oldest surviving stone castle in Britain. The castle was established by William FitzOsbern immediately after the Norman conquest, and was extended in later centuries before becoming ruined after the Civil War. A Benedictine priory was also established within the walled town, which was the centre of the Marcher lordship of Striguil. The port of Chepstow became noted in the Middle Ages for its imports of wine, and also became a major centre for the export of timber and bark, from nearby woodland in the Wye Valley and Forest of Dean. In the late eighteenth century the town was a focus of early tourism as part of the "Wye Tour", and the tourist industry remains important. Other important industries included shipbuilding – one of the First World War National Shipyards was established in the town – and heavy engineering, including the prefabrication of bridges and wind turbine towers. Chepstow is also well known for its racecourse, which has hosted the Welsh National each year since 1949. The town had a population of 10,821 according to the 2001 census, increasing to 12,350 at the 2011 census. It is served by the M48 motorway, and its accessibility to the cities of Bristol, Newport and Cardiff means it has a large number of commuters. It is administered as part of Monmouthshire County Council, and is within the Monmouth UK parliamentary constituency and Senedd constituency. 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. The population of the built-up area including these villages was 16,169 in 2011.

Chepstow Rural District was a rural district in the administrative county of Monmouthshire, Wales. It was established under the Local Government Act 1894, and was abolished in 1974 when its functions were assumed by the new Monmouth District Council. The responsibilities of the Rural District Council included housing, sanitation, sewerage, water supply, refuse collection, road maintenance, cemeteries, parks, and licensing of public entertainments. The council's area covered the civil parishes of Caerwent, Caldicot, Devauden, Kilgwrrwg, Llanfihangel nigh Rogiet, Llangwm, Mathern, Portskewett, Rogiet, St. Arvans, Shirenewton, Tintern and Undy. The town of Chepstow itself fell under a separate urban district. The Rural District Council was particularly involved in the development of Caldicot as a town. In the 1950s it decided that the village should be allowed to double its existing size, to reach a population of about 3,000. Soon afterwards, the government decided to build a new steelworks at Llanwern, and its expansion plans were revised upwards, so that, by the late 1960s, Caldicot had a population of over 7,000. In 1963, the Council bought Caldicot Castle from the Cobb family for £12,000.

The Powis Almshouses are a block of almshouses in Chepstow, Monmouthshire, Wales, at the junction of Church Street and Bridge Street (formerly St Anne's Street). The building dates from about 1721, and was constructed as a result of a bequest from Thomas Powis, a vintner who was probably born in the town. The almshouse is a Grade II* listed building.

Chepstow Castle (Welsh: Castell Cas-gwent) at Chepstow, Monmouthshire, Wales is the oldest surviving post-Roman stone fortification in Britain. Located above cliffs on the River Wye, construction began in 1067 under the instruction of the Norman Lord William FitzOsbern. Originally known as Striguil, it was the southernmost of a chain of castles built in the Welsh Marches, and with its attached lordship took the name of the adjoining market town in about the 14th century. In the 12th century the castle was used in the conquest of Gwent, the first independent Welsh kingdom to be conquered by the Normans. It was subsequently held by two of the most powerful Anglo-Norman magnates of medieval England, William Marshal and Richard de Clare. However, by the 16th century its military importance had waned and parts of its structure were converted into domestic ranges. Although re-garrisoned during and after the English Civil War, by the 1700s it had fallen into decay. With the later growth of tourism, the castle became a popular visitor destination. The ruins were Grade I listed on 6 December 1950.

Striguil or Strigoil is the name that was used from the 11th century until the late 14th century for the port and Norman castle of Chepstow, on the Welsh side of the River Wye which forms the boundary with England. The name was also applied to the Marcher lordship which controlled the area in the period between the Norman conquest and the formation of Monmouthshire under the Laws in Wales Acts 1535–1542.

Castle Terrace, originally known as Castle Parade, is an unbroken row of fourteen three-storied Georgian dwellings in Chepstow, Monmouthshire, Wales. The backs of the houses face Chepstow Castle. The whole terrace, numbers 33A–47 Bridge Street, is a Grade II* listed building.

St Mary's is the name of an electoral ward in the town of Chepstow, Monmouthshire, Wales. The ward elects councillors to Chepstow Town Council and Monmouthshire County Council.

The Parish and Priory Church of St Mary is located in Chepstow, Monmouthshire, south east Wales. Parts of the building, including its ornate west doorway, date from the late 11th century and are contemporary with the nearby Norman castle. The church is a Grade I listed building.