Piercefield House

The Green Gathering, formerly known as the Big Green Gathering is a festival with an environmental and social justice focus, including workshops and talks on permaculture, politics, ecology and crafts, as well as art, live music and spoken word performances. The first Big Green Gathering was held in 1994 and the festival is currently held in Chepstow, Monmouthshire although it has previously been held in various locations in Somerset and Wiltshire, England.

Otter Hole is perhaps one of the best decorated caves in Britain. Located on the Wales–England border just north of Chepstow, the cave runs from the banks of the tidal River Wye under the Chepstow Racecourse and onwards through various chambers, each rich with cave formations. Because of its importance as one of the finest examples of decorated caverns in Europe, access is restricted and is managed by the Royal Forest of Dean Caving Club on behalf of the landowner.

Chepstow Racecourse is a thoroughbred horse racing course located just north of the town of Chepstow in Monmouthshire, Wales, near the southern end of the Wye Valley and close to the border with England. It is one of 16 racecourses operated by the Arena Racing Company and is home of the richest race in Wales, the Coral Welsh Grand National.

Lancaut (Welsh: Llan Cewydd) is a deserted village and former civil parish, now in the parish of Tidenham, in the Forest of Dean district, in Gloucestershire, England, located alongside the River Wye, around two miles north of Chepstow. It occupies a narrow-necked promontory formed by a curve of the river, which acts as the border between England and Wales. Little remains of the village today, except for the roofless church of St. James.

The Wyndcliff or Wynd Cliff (historically sometimes spelt Wyndcliffe) is a steep limestone cliff rising above the western bank of the River Wye in Monmouthshire, Wales, some 1 mile (1.6 km) north-east of the village of St Arvans, 2.5 miles (4.0 km) south of Tintern, and 3.5 miles (5.6 km) north of the town of Chepstow, within the Wye Valley Area of Outstanding Natural Beauty. The cliff rises to 771 feet (235 m) at its summit, the highest point on the Monmouthshire bank of the Wye. The area is traversed by the Wye Valley Walk, and is also a popular venue for rock climbing. Access is provided by the A466 road which passes along the valley immediately below the cliff face. The site has been appreciated by visitors since the time of the Wye Tour in the late eighteenth and early nineteenth centuries. It contains several viewing points constructed so that visitors can gain a full appreciation of the area's Picturesque landscape, including the Eagle's Nest viewpoint which was built in 1828 for its landowner the Duke of Beaufort as an extension to the walking path network already developed around the nearby Piercefield estate. It has been described as "one of the most impressive viewpoints in the British Isles".

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.

Wintour's Leap is a noted rock climbing location and viewpoint. It is located near the village of Woodcroft in Gloucestershire, on the English side of the Wye Valley, north of Chepstow.

The Old Wye Bridge or Town Bridge at Chepstow, also known historically as Chepstow Bridge, crosses the River Wye between Monmouthshire in Wales and Gloucestershire in England, close to Chepstow Castle. Although there had been earlier wooden bridges on the site since Norman times, the current road bridge was constructed of cast iron in 1816 during the Regency period, by John Rastrick of Bridgnorth, who greatly modified earlier plans by John Rennie. The bridge crosses a river with one of the highest tidal ranges in the world. It carried the main A48 road between Newport and Gloucester until 1988, when a new road bridge was opened downstream alongside Chepstow Railway Bridge. The road bridge now carries local traffic between Chepstow and Tutshill. It is a Grade I listed building.

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 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.

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.

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.