Chepstow sits on the River Wye, about 2 miles upstream of its confluence with the River Severn. The location was named Striguil (or Estrighoiel) in Norman times - from the Welsh word ystraigyl meaning a bend in the river - but by about the 14th century had become known in English as Chepstow, from the old English ceap / chepe stowe meaning market place. The Welsh name for the town, Cas-gwent (being short for Castell Gwent), means "castle of Gwent", the name Gwent itself deriving ultimately from the Roman name Venta applied to what is now called Caerwent, some 5 miles west of Chepstow.
The oldest known site of human habitation around Chepstow is at Thornwell, near the modern 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. There are also Iron Age fortified camps in the area, at Bulwark and Piercefield, dating from the time of the Silures. Later, there was probably a Roman bridge or ford over the Wye at Castleford about 1 mile upstream of the existing town bridge Chepstow is located at a crossing point directly between the Roman towns at Gloucester (Glevum) and Caerwent (Venta Silurum). Although historians think it likely that there was a small Roman fort in the area, the only evidence found so far has been of Roman material and burials, rather than buildings
After the Romans left, Chepstow replaced Caerwent as the main port and market town within the southern part of the Kingdom of Gwent. A priory was established during this period, dedicated to St. Cynfarch (alternatively Cynmarch, Kynemark or Kingsmark) a disciple of St. Dyfrig. Few remains have been found of the priory, which was located in the area originally called Llangynfarch, now a suburban housing estate (Kingsmark Lane). It became an Augustinian priory but was eventually superseded by the later Norman priory in the town centre
The town is close to the southern end of Offa's Dyke, which begins at Sedbury near the east bank of the Wye and runs all the way to the Irish Sea at Prestatyn in north Wales. This was built in the 8th century as a boundary between English and Welsh kingdoms, although recent research suggests that the part near Chepstow may not actually be part of the original Dyke. The Lancaut and Beachley peninsulas, opposite Chepstow, formed part of Gwent rather than Mercia at that time, although the position was reversed by the time of the Domesday Book, in which Striguil is included as part of Gloucestershire.
Chepstow town centre has over 130 shops within walking distance of 1000 car park spaces. There are 16 hotels, bars and pubs, and 15 restaurants and cafes Chepstow Community Hospital was opened in 2002 as a PFI-funded hospital and several new housing estates have been developed across the town. Over £2 million has recently been invested in regenerating the town centre. This scheme, which includes new sculptures including a boatman and other public art, encountered some local criticism over its high cost, but has gained several national awards reflecting its high design quality.
The area beside the river has been attractively landscaped as part of a flood defence scheme. The town holds a biennial festival, an annual folk festival, and has also organised major son et lumiere pageants covering aspects of local history, using local residents under professional direction. There is also a local museum, opposite Chepstow Castle entrance.
There are industrial estates at Bulwark and close to the railway station, and a distribution centre on the edge of the town adjoining the junction with the M48 motorway. There has been housing development in recent years, particularly at the Bayfield estate west of the A466.
Chepstow Racecourse is the leading horse racing facility and course in Wales. It is located on the edge of the town, in the grounds of the ruined Piercefield House. Sundays see a large market set up on the racecourse grounds which is attended by vendors from as far afield as Birmingham, London, Kent and beyond. During the course of the year the racecourse hosts hobby and antique fairs.
Chepstow also has many schools, including Chepstow School. J.K. Rowling is an alumna of Wyedean School and Sixth Form Centre in nearby Sedbury. There are also a number of churches in Chepstow, including non-conformist denominations.
Chepstow Town AFC currently play in Division One of the Gwent County LeagueThey last won the league title in 1997. The town also has a rugby football club and an athletic Club for tennis, bowls, cricket and junior football.
Nearby are the Royal Forest of Dean, the Wye Valley, and the National Diving and Activity Centre. Tintern Abbey is about 5 miles distant. Some residents of the town commute to Bristol, Newport, Cardiff and elsewhere.
Chepstow is twinned with Cormeilles, France.
All Sources from wikipedia.com