Chepstow has over 130 shops within easy walking distance of 1000 car park spaces. There are 16 Hotels, Bars and Pubs, and 15 Restaurants and Cafes.

Chepstow sits upstream of the confluence of the River Wye and River Severn. There has been a settlement on the site since at least the early Middle Ages. It was named Striguil in Norman times - from the Welsh word ystraigyl meaning a bend in the river - but became known as Chepstow from the old English ceap / chepe stowe meaning market place.

The oldest areas of known habitation are the Iron Age fortified camps at Bulwark and Piercefield. Later, there may have been a Roman bridge or ford over the Wye, either near the existing bridge or about 1 mile upstream at Castleford. Chepstow is located at a crossing point directly between the Roman towns of Gloucester and Caerwent. The town is also close to the southern point of Offa's Dyke, which begins on the east bank of the Wye and runs all the way to the Irish Sea in north Wales. This was built in about the 8th century as a boundary between English and Welsh kingdoms.

Chepstow Castle is the oldest surviving stone fortification in Britain. After the Norman Invasion Chepstow was identified as an ideal site for a castle, as it not only controlled a crossing point on the River Wye, but also because the steep limestone gorge and castle dell afforded an excellent defensive location. William the Conqueror ordered its construction in 1067, and, according to the Domesday Book, it was designed by the master castle builder of the time, William fitzOsbern. The speed with which William the Conqueror committed to the creation of a castle in Chepstow is testament to its strategic importance. At the time, the kingdoms in the area were independent of the English crown and the castle in Chepstow provided a way to suppress the Welsh from attacking Gloucestershire. From the 14th century, with the end of the wars between England and Wales, the castle's importance declined.

A town grew up beside the castle, the Priory church, and the port, and in 1294 Chepstow was given the right to hold a weekly market and annual fair. It flourished partly because it was exempt from English taxation. The town wall, locally known as the Port Wall, was built about this time, and mostly still stands. The Town Gate through the wall at the top end of the High Street was rebuilt in the 16th century and was used as a toll gate.

The most significant church in Chepstow is the Parish and Priory Church of St Mary, located at the bottom of the town. It, like the castle, is Norman in origin, although much rebuilt and extended in later centuries. St Mary's was the centre of a religious community with a convent and school, the remains of which are buried under the adjoining car park. Benedictine monks from Cormeilles in Normandy, Chepstow's twin town, were there until the Dissolution of the Monasteries from 1536.

The town today:

Over £2 million has recently been invested in regenerating the town centre. This scheme, which includes new sculptures and other public art has gained several national awards reflecting its high design quality. The new design has encouraged the development of a wide calender of events in the town centre including Art on the Railings, The Two Rivers FolkFestival, Continental Market, Hoggin the Bridge, WI Market, Local Farmers Market and much more.

The town centre has a good range of shops, pubs and restaurants. The area beside the river has been attractively landscaped as part of a flood defence scheme. The town holds a biennial festival, and in most recent years has also organised major son et lumiere pageants covering aspects of local history, using local residents under professional direction. There is also an excellent local museum, opposite the Castle entrance.

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 an extensive 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 a number of hobbies and antique fairs.

Chepstow also has many excellent schools including Chepstow School. One of the best co-education semi-boarding schools St Johns on the Hill is located on the outskirts towards Tutshill. There are also a number of churches in Chepstow, including a variety of non-conformist denominations.

Nearby are the Royal Forest of Dean and the Wye Valley. Tintern Abbey is about 5 miles distant. Chepstow is twinned with Cormeilles.