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.

However, the name used by the Normans for the castle and lordship was Striguil (in various spellings, such as Estrighoiel), probably derived from a Welsh word ystraigyl, meaning a bend in the river.

[3] The earliest recorded evidence of human activity in the Chepstow area are charcoal deposits, found in St Peter's Cave, at the base of Hardwick Cliff, Bulwark, dating from the Upper Paleolithic.

To the north of the modern town centre, a small church was established dedicated to St. Cynfarch (alternatively Cynmarch, Kynemark or Kingsmark), a disciple of St. Dyfrig.

[10] The town is close to the southern point of Offa's Dyke, which begins on the east bank of the Wye at Sedbury and runs all the way to the Irish Sea in north Wales.

This was built in the late 8th century as a boundary between Mercia and the Welsh kingdoms, although some recent research has questioned whether the stretch near Chepstow formed part of the original Dyke.

Chepstow Castle was founded by William fitzOsbern, 1st Earl of Hereford, in 1067, and its Great Tower, often cited as the oldest surviving stone fortification in Britain, dates from that time or shortly afterwards.

Bigod was also responsible for establishing a weekly market and annual fair, in the town which had grown up on the slopes between the castle and priory, and for building the Port Wall around it shortly after 1274.

[3] The port of Chepstow developed during the mediaeval period, one reason being that its control by a Marcher Lord, rather than by the King, meant that it was exempt from English taxation.

From mediaeval times, Chepstow was the largest port in Wales; its ships sailed as far as Iceland and Turkey, as well as to France and Portugal, and the town was known for its imports of wine.

The port continued to flourish; during the period 1790 to 1795, records show a greater tonnage of goods handled than Swansea, Cardiff and Newport combined.

Chepstow reached the peak of its importance during the Napoleonic Wars, when its exports of timber, for ships, and bark, for leather tanning, were especially vital.

Many buildings in the town remain from the late 18th and early 19th centuries; the elegant cast iron bridge across the Wye was opened in 1816 to replace an earlier wooden structure.

Visitors regularly took boats from Ross-on-Wye and Monmouth down the river, visiting, drawing and painting the "picturesque" views of the area, which included those of Tintern Abbey, Piercefield House, and the ruined Chepstow Castle.

[8] The port's trade declined after the early 19th century, as Cardiff, Newport and Swansea became more suitable for handling the bulk export of coal and steel from the Glamorganshire and Monmouthshire valleys.

The town developed rapidly after the opening of the Severn Bridge in 1966, which replaced the car ferry between Beachley and Aust and allowed easier commuting between Chepstow and larger centres including Bristol and Cardiff.

[18] The bedrock of Chepstow is limestone, mudstone and sandstone, overlain in places with some gravels and the clay and silt of the river's tidal flats, which are of marine origin and up to two million years old.

The rock of Sedbury cliffs and those under Chepstow Castle are Carboniferous Limestone, hundreds of metres thick in the area, made of particles and shells of sea creatures from 330 to 360 million years ago.

[19] Layered outcrops of darker Black Rock Limestone, which makes up a broad part of Chepstow's bedrock, are very clear in cliffs along Craig yr Afon, part of the Wales Coast Path extending from Wye Crescent, and by the link road from Bulwark Road to the M48, where the looser reddish Mercia Mudstone (which extends under Bulwark and Sedbury and forms the cliffs at the Severn) and the lighter Hunts Bay limestone are also seen.

In July 2015, the company announced that the site was to close with the loss of 125 jobs, following the decision by the UK government to end subsidies for onshore wind generation.

Its location at the southern end of the Wye Valley, together with its own sights including its castle and racecourse, have contributed to its development as a tourist centre.

Since 2012, an annual series of "Castell Roc" music events has been held inside Chepstow Castle each August, featuring performances by artists such as Leo Sayer, Dr Hook, Bad Manners, and Jools Holland.

[57] Chepstow has no dedicated cinema or theatre, although film showings, theatrical and other events regularly take place in the Drill Hall, close to the Castle and riverside area.

As of 2017 the team play in Division Three East A of the WRU National League The town also has an athletic Club for archery (St Kingsmark Bowmen), tennis, bowls, cricket and junior football.

The town centre itself features stone carvings, artworks, and information plaques placed in the pavement and walls, installed as part of a regeneration scheme in 2004/05; they illustrate Chepstow's history.

[82][88] Chepstow Racecourse was opened in 1926 in the grounds of Piercefield House, 1 mile (1.6 km) north of the town centre on the road towards Tintern.

[92] James Stephens (1821–1889), a stonemason who was a supporter of the Chartists and later an influential Australian trade unionist, was born in the town,[93] as was Sir Isambard Owen (1857–1927), a physician who became an academic and a leading figure in the formation of the University of Wales.

[94] John Fitchett Marsh (1818–1880), who had been responsible for establishing the first municipal library at Warrington, retired to Hardwick Court at Chepstow in 1873 and wrote on the history of the castle.

Fulford (1859–1929), born in Chepstow of Australian parents, joined the British Foreign Service and for several decades occupied important consular posts in China.