Chepstow Racecourse

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.

Piercefield House is a largely ruined neo-classical country house near St Arvans, Monmouthshire, Wales, about 1.5 miles (2.4 km) north of the centre of Chepstow. The central block of the house was designed in the very late 18th century, by, or to the designs of, Sir John Soane. It is flanked by two pavilions, of slightly later date, by Joseph Bonomi the Elder. The house sits within Piercefield Park, a Grade I listed historic landscape, that was created in the 18th century as a notable Picturesque estate. The estate has links to colonialism and slavery. After long ownership by the Walter family, in 1740 it was bought by Valentine Morris, a slaver and planter from Antigua. His son, also Valentine, developed the park and grounds into one of the 18th century’s most famous Picturesque landscapes. His prodigality ruined him, and the estate was sold to a banker, George Smith, who began the present house. He was in turn bankrupted and Piercefield was bought by Sir Mark Wood, a nabob who had made his fortune in Bengal. In 1802, the estate was bought by Nathaniel Wells, son of William Wells, a slaver from Saint Kitts, and Juggy, later Joardine Wells, his enslaved house servant. Nathaniel and his mother both received their freedom and he inherited the bulk of his father’s wealth. Establishing himself at Piercefield, Nathaniel Wells became, in turn, a Justice of the Peace, a Lieutenant in the Chepstow Yeomanry, and Deputy lieutenant and High Sheriff of Monmouthshire, a notable series of firsts, or near firsts, for a black man in Georgian England. The house is now a shell, along with its extensive stable block, but its status as a Grade II* listed building reflects its importance. It is currently owned by the Reuben brothers, London-based property developers. A campaign to save and restore the building was launched by SAVE Britain's Heritage in 2013. The house has been repeatedly marketed for sale since the early 2000s but no sale has been concluded. Despite emergency stabilising work in 2008/9, the condition of the house continues to deteriorate.

St. Arvans (Welsh: Sain Arfan or Llanarfan) is a village and community (equivalent to a parish) in Monmouthshire, south-east Wales. It is located two miles north west of Chepstow, close to Chepstow Racecourse, Piercefield House and the Wye Valley AONB. It is connected by a segregated bicycle path to the edge of Chepstow.

Chepstow Community Hospital (Welsh: Ysbyty Cymunedol Cas-gwent) is a community hospital located on the east side of St Lawrence Road in Chepstow, Monmouthshire, Wales. It is managed by the Aneurin Bevan University Health Board.

St Lawrence Hospital (Welsh: Ysbyty St Lawrence) was a specialist plastic surgery and burns hospital on the west side of St Lawrence Road in Chepstow, Wales.

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.

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".

Wyndcliffe Court, 0.5 miles (0.80 km) north of the village of St. Arvans, Monmouthshire, Wales, is a Grade II* listed country house and gardens in the Arts and Crafts style, completed in 1922. The client was Charles Leigh Clay and the architect Eric Francis. The gardens were designed by Henry Avray Tipping and are included on the Cadw/ICOMOS Register of Parks and Gardens of Special Historic Interest in Wales.

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.

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.