Chepstow, Cas-gwent in the Welsh language, has been an important place for many reasons. Just one year after the Norman invasion, led by William the Conqueror in 1066, the foundations of the town’s impressive castle were laid down by William FitzOsbern, Knight of Cormeilles. Don’t miss the chance to visit the oldest surviving stone castle in Britain, the southernmost of a chain of castles along the Marches constructed to defend and control the border between England and Wales. St Mary’s Priory Church was built around the same time and well worth a visit. In 1975, many years later, Chepstow became twinned with Cormeilles, a pretty, rural town in Normandy.
Wherever you walk in Chepstow you are likely to hear the sound of seagulls, reminding you that you are close to what was once a busy port. In the Middle Ages, imported wine was off-loaded on its quayside. By the 18th century, it had become a major centre for the export of timber and bark from the Wye Valley and Forest of Dean. During the First World War, National Shipyard No. 1 was established at Chepstow and over 6,000 skilled workers came to the area from all over Britain. You will still see plenty of evidence of the town’s maritime history if you wander along the riverside to The Back.
Horse racing and a wide range of other events are held throughout the year at Chepstow Racecourse, which is home to the Coral Welsh Grand National. There has been horse-racing here since the late 19th century. St. Pierre Marriott Hotel & Country Club has one of the finest and most picturesque golf courses in the country and for many years was host to the British (formerly Dunlop) Masters tournament which attracted some of the top players in the world.
Chepstow stages a number of festivals including, the Castell Roc music festival held in the castle during the summer and the Chepstow Festival of Arts. Historically, the town has been home to the Chepstow Wassail and Mari Lwyd. This is an unusual border festival featuring Welsh traditions dating back many years, involving the blessing of apple trees, decorated and shrouded horse skulls and border morris-dancing.
As well as shopping, history and sports, Chepstow is also a Walkers Are Welcome town, home to many beautiful walks. Of national importance, is the Wales Coast Path which starts and finishes at the riverfront. If combined with Offas Dyke Path, this allows you to walk all around Wales. The Wye Valley Walk to Plynlimon starts/finishes at the Castle. The Gloucestershire Way to Tewkesbury and the Monmouthshire Way also starts/finishes at Chepstow.
Did you know that Chepstow is home to some amazing bridges?
Chepstow Bridge (known locally as the Old Wye Bridge), is the World's largest iron arch road bridge from the first 50 years (1780-1830) of iron and steel construction. Designed by John Rastrick, the now Grade 1 listed bridge was first opened on the 24th July 1816, and is an architectural marvel and feat of engineering. It forms a boundary between Wales and England such that if you walk to the middle, you can actually stand with one foot in England and one foot in Wales – this makes for a great photo!
Chepstow railway bridge was built to the instructions of Isambard Kingdom Brunel in 1852. The "Great Tubular Bridge," over the River Wye at Chepstow, which at that point forms another boundary between Wales and England.
The Severn Bridge (Pont Hafren in Welsh), is a motorway suspension bridge that spans the River Severn between South Gloucestershire in England and Monmouthshire in South East Wales. It is the original Severn road crossing between England and Wales. It took three and a half years to build at a cost of £8 million. It replaced the old Aust Ferries – the Severn King, Queen and Princess, that previously carried vehicles and passengers across the river. The Severn Bridge was opened in 1966 by Queen Elizabeth II. For thirty years, the bridge carried the M4 motorway. It was granted Grade I listed status in 1999.
The Second Severn Crossing (Ail Groesfan Hafren in Welsh), officially renamed the Prince of Wales Bridge (Welsh: Pont Tywysog Cymru) since July 2018, is the M4 motorway bridge over the River Severn between England and Wales, inaugurated on 5 June 1996 by the Prince of Wales to supplement the traffic capacity of the Severn Bridge built in 1966. It is further southwest than the Severn Bridge but can easily be seen whilst crossing the Severn Bridge and from other parts of town.