Old Wye Bridge, Chepstow

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.

The Gloucester Hole is a roughly square opening in the limestone cliffs of the River Wye, directly opposite the town of Chepstow. The hole itself is on the Tutshill side of the river, in Gloucestershire, England; the river forms the boundary with Wales. The small square opening leads into a much larger chamber within the cliffs. The entrance is about 5 feet 6 inches (1.7 m) square, and runs in for about 12 feet (3.7 m). The cave was a natural opening in the limestone which was enlarged so that its greatest depth and greatest breadth are 27 feet (8.2 m), and its height at one point is 15 feet (4.6 m). There is speculation about its origin and about what it has been used for in the past. Suggestions include its use by the Shirenewton Quakers for storing tea, or for the storing of explosives by Brunel when the railway was built. A local antiquarian, J.G. Wood, wrote in 1901 that nearly 50 years earlier he had quizzed the oldest inhabitants and discovered that this natural cave had been enlarged and fitted with a crane at its mouth to unload large ships that could moor there in deep water, but could not easily dock at the shallower wharves on the Chepstow side of the river. The cargo was then reloaded onto trows and taken up river to Monmouth and Hereford. For many years mooring chains and rings in the cliff below survived to support this explanation. The cave can only be reached by boat at high tide.Next to the Hole is a Union Flag which was first painted in 1935 to mark the Silver Jubilee of King George V by some Chepstow salmon fishermen, and is regularly repainted. The highest tides reach nearly to the top of it. During flooding in January 2014, the water level rose above the flag for the first time in many years.

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.

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.

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.

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.

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.

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.

Chepstow Railway Bridge was built to the instructions of Isambard Kingdom Brunel in 1852. The "Great Tubular Bridge" over the River Wye at Chepstow, which at that point forms the boundary between Wales and England, is considered one of Brunel's major achievements, despite its appearance. It was economical in its use of materials, and would prove to be the design prototype for Brunel's Royal Albert Bridge at Saltash. Although the superstructure has since been replaced, Brunel's tubular iron supports are still in place. It is a Grade II listed structure.

Chepstow railway station is a part of the British railway system owned by Network Rail and is operated by Transport for Wales. Chepstow station is on the Gloucester to Newport Line, 141 miles 33 chains (227.6 km) from the zero point at Paddington, measured via Stroud. It is 330 yards (300 m) from the town centre, at Station Road. Chepstow is a historic walled border town and ancient port, situated at the southern end of the Wye Valley, two hours from London. The line continues east from the station to Gloucester over the Chepstow railway bridge. It was formerly the junction station for the Wye Valley Railway to Monmouth Troy station until this line closed to passengers in 1959. The railway now consists of a double track line with a trailing crossover to the east of the station, plus some disused track in the former yard.