The oldest known habitation at Chepstow is on the southern edge of the town, overlooking the estuaries of the Wye and Severn, where archaeological investigations revealed continuous human occupation from the Mesolithic period of around 5000 BC until the end of the Roman period at around 400 AD.

We found Chepstow to be a very pleasant town and this view is of High Street.

Chepstow Castle was founded in 1067, and its Great Tower, often cited as the oldest surviving stone fortification in Britain, dates from around that time. Its site, with sheer cliffs on one side and a natural valley on the other, afforded an excellent defensive location.

It certainly looks impressive and it turned out to be a very large castle.

Chepstow was given its first charter in 1524, and became part of Monmouthshire when the county was formed. Many buildings in the town remain from the late 18th and early 19th centuries and the elegant cast iron bridge across the Wye was opened in 1816 to replace an earlier wooden structure.

Much of Chepstow's late-13th-century Port Wall remains intact and is best seen adjoining the main town car park in Welsh Street or beside the main A48 road at the top of School Hill. It can also be seen adjoining the Gate House, which was built in 1609 beside the Town Gate at the top (western) end of the High Street.