Walk 48: Chepstow Town Walk: A Christmas stroll

The ‘Needs to Know’

Distance: Probably just over 1 mile (1.61 km)

Time to walk: Depends whether you want to have a closer look at the castle or take in some of the area across the river

Difficulty: All on hard paths

Parking: The walk starts at the Castle Car Park (Pay & Display)

Public toilets: Plenty of bars & cafes

Map of the route: None, but it’s only a small area

This is a short walk around the centre of lovely Chepstow plus the riverside area looking at the history of the town. We’ve visited Chepstow several times over the years, camping on the finishing straight at the Racecourse & going slightly more upmarket at St Pierre Golf & Country Club

So what can we tell you about Chepstow?

Chepstow (Welsh: Cas-gwent) lies in Monmouthshire, Wales, adjoining the border with Gloucestershire, England. The name Chepstow derives from the old English ceap / chepe stowe, meaning market place or trading centre. The word “stow” usually denotes a place of special significance & the root “chep” is the same as that in other place names such as Chipping Sodbury & Cheapside. The Welsh name Cas-gwent refers to the “castle of Gwent”

There’s been continuous human occupation from the Mesolithic period around 5000 BC. There are Iron Age fortified camps in the area & the Romans & the Normans also had significant presence. The town developed rapidly after the opening of the Severn Bridge in 1966, which replaced the car ferry between Beachley & Aust & allowed easier commuting between Chepstow & larger centres including Bristol & Cardiff. Chepstow developed from medieval times as a port and trading centre. Its port functions, together with its shipbuilding industry, have now virtually ceased

We’ll look at the impressive castle & more of the history en route

So…Let’s Walk!

1. We left the car in Castle car park, got out & admired the huge Chepstow Castle…



You can’t really get the full size of the Castle from the carpark. Chepstow Castle is often described as the oldest surviving stone castle in Britain. The castle was established by William FitzOsbern immediately after the Norman conquest, & was extended in later centuries before becoming ruined after the Civil War. It’s unique as it was built in a narrow shape along the edge of the cliff rather than in the traditional round format

We couldn’t get a snap from the right angle today so have included a published picture to show it’s true size & precariousness!


2. Head out of the carpark into Bridge Street, turning right up the hill…

It's ben a heavy night!

It’s been a heavy night!


3. The first place of note is Cromwell House on the left…



The name reflects a claim that Oliver Cromwell slept in the house after taking Chepstow in 1648.  It’s now a pottery & gallery, home of local artist David Jones who’s noted for his paintings of the Wye Valley

4. Next door is a quiet, almost hidden, little public garden known as Hollins Close Garden. Enter & spend a few moments in it…



On the right, heading up the hill, is a terrace of 15 impressive bow windowed houses



5. At the top of Bridge Street on the right are Powis Almshouses…


Thomas Powis was probably born in Chepstow in or about 1675, the son of Grevill Powis who may have been attached to the garrison at Chepstow Castle. Nothing is known of Thomas Powis’ later life other than that, in 1716, he was a vintner in Enfield, Middlesex, & in his will gave £1,800 to establish an almshouse in Chepstow for twelve poor men & women. He died in 1716, but because of legal ambiguities over the interpretation of the will it was not settled until 1718. Applicants for accommodation were required to have been resident in Chepstow for three years, be of good character, & to be able to support themselves financially. Residents were expected to keep their rooms “clean & in neat order” & to behave responsibly. Several residents were removed from their rooms for misdemeanours including drunkenness, rioutous & improper behaviour, & in one case in 1847 for “admitting an improper woman into his room”

6. Bear left down Upper Church Street. Interestingly, there’s a modern sheltered housing property for the elderly on the left – perhaps the new Powis


There’s some more Almshouses on the left here…Montague Almshouses


Sir Walter Montague, who died in 1615, left provision for these almshouses in his will. They originally housed 5 men & 5 women, but the properties were rebuilt after the Second World War, preserving part of the original facade

Montague actually has a link with our own Northamptonshire as his father was Lord of the Manor at Hanging Houghton

7. Turn right up the pedestrianised & delightful St Mary Street…


St Mary Street contains many small independent shops & a cracking chinese restaurant…Shangri-La


We can also recommend the excellent Bellhanger pub which is huge & part of the Wetherspoon chain. In the past Chepstow was known for bell hanging

This pub was once two shops, one of which was a ironmonger, bell hanger & nailer


Keep out of here!

Keep out of here!

8. The top of St Mary Street opens out into Beaufort Square & the High Street


We’ll look at Beaufort Square in more detail later as we come back down the other side. For now continue straight up the hilly High Street



9. Spotted the turret further up on the left? This is Chepstow’s famous department store…Herbert Lewis’. The building’s called the ‘Coronation Buildings’ & was built by the family



This store is one of the oldest department stores in the UK, established in 1878 by Herbert Lewis & still managed by the same family – now in it’s fifth generation

Fabulous clock

Fabulous clock

10. At the top of the High Street’s The Town Gate…


The Town Gate at Chepstow, Monmouthshire, Wales, was historically the only landward entrance to the town through the Port Wall & a point to collect tolls from those coming to the town with animals & produce for the market. It was originally built, with the wall, in the late 13th century. The current archway mainly dates from the 16th century, but has been restored & partly rebuilt on several occasions. It originally had a gate, portcullis & guardroom

11. To the left of the Gate is The Gatehouse…


The Gate House adjoining the Town Gate was rebuilt in 1609 for Margaret Cleyton, a wealthy widow & benefactor. Her elaborate tomb is in St Mary’s Church. The building was later used as a brewery, farmhouse, surgery & bank, before being presented to the town in 1919 by J.H. Silley, an engineer who was influential in bringing the National Shipyard No.1 to the town in the First World War. It then became the offices of Chepstow Urban District Council & is now used by the Town Council & Citizens’ Advice Bureau

The elaborate inscription in the wooden doorframe commemorates the rebuilding…



12. Cross over the High Street into White Lion Square which contains The White Lion pub & an Italian restaurant…


The George Hotel was originally built on this site by Margaret Cleyton in about 1620. It later became one of the town’s main coaching inns. The building was completely destroyed by fire in May 1896, but was rebuilt & reopened in 1899. The area outside the Gate was once where those unwilling to pay the lord’s dues did their trading. A stone cross known locally as “Robin Hood’s Cross” existed outside the George until it was dismantled in 1759. Trading took place in the streets here until a new livestock market was built elsewhere in the town in 1893

13. Walk a little way down Bank Street & turn left through Manor Way shopping centre…



…passing the library & information centre


14. At the top of the slope is the town’s main car park which also contains a stretch of the town wall known as The Portal, where at the far end you get a good view over the Castle


After finishing admiring the wall retrace your steps through the shopping centre to Bank Street



15. Follow Bank Street back down to Beaufort Square where we promised we’d return..



This was once the centre of Chepstow & where later tonight the Xmas decorations & Carol Singers did the town proud

IMG_5162 copy

16. Firstly love the sculptures here…



The War Memorial is pretty impressive…


…as next door is the gun from a captured German World War I submarine…



King George V presented it to the town to remember Able Seaman William VC, a Chepstow man killed in the Gallipoli landing

17. There’s some different types of buildings in the square including the now Costa shop with the wrought iron railings…


To exit the Square take the left route down Hocker Hill Street


18. On the left here’s a house called St Maur where Admiral Nelson once stayed. At the time it was an inn


19. Keep left down the picturesque & fabulous Hocker Hill Street with its cobbles


The buildings along here are 18th & 19th century with more bow windows & superb door frames. At the bottom’s the rather interesting Five Alls Inn which has a very interesting pub sign…



20. Just past the pub on the left’s a very small arched doorway which led to a wine cellar below the Powis Almshouses. Apparently there was once a thriving wine trade in the town



Continue straight back down Bridge Street passing where we started this walk!




21. Let’s take a look at the other establishments around here…

On the left’s The Three Tuns


The Three Tuns dates back to the early 1600’s & has been a public house for a large majority of its time.

The description of the pub in a sale publication in 1899 is as follows: ” The Three Tuns was ‘entered by a broad stone-flagged passage’ & contained ‘Living Room, Large Bar, Back Kitchen & loft over also spacious Cellar’. On the first floor were three bedrooms & the pub adjoined a cottage, stabling a trap house & a yard ith ‘a gate opening on the the Castle Entrance”

A tun is a large cask for wines & other liquids with a capacity of two pipes or four hogsheads or 282 old wine gallons.


Next on the right’s the Chepstow Castle Inn


22. Next door’s Chepstow’s Museum which we didn’t get time to visit as were working during their opening hours…


Chepstow Museum displays the towns wine trade, shipbuilding & salmon fishing  industries as well as photographs, programmes & posters recalling the pastimes of local people. The 18th & 19th century paintings & prints show great aspects of Chepstow & the Wye Valley to artist. The building is named Gwy House & used to be the home of wealthy merchant families & was once also a hospital

23. Carry straight on but, if you can afford it call in for dinner at the award winning Afon Gwy Restaurant – doesn’t appear to have a website though



24. We should be heading straight on across The Old Wye Bridge now, but it’s closed to traffic so firstly turn right along St Ann’s Street to have a quick look at some well preserved 17th century properties…


25. Track back & luckily the bridge is still open to walkers instead of traffic. There’s an interesting pub on the right called The Bridge Inn



Not sure whether it’s open at the moment tho…but love the sign on the wall as it’s so true as we’ll see when we cross the Wye


26. The old Wye Bridge, when not covered in scaffolding is beautiful as we’ve shown below…

Here's how it looked today

Here’s how it looked today

And here's how it should look!

And here’s how it should look!

Although there had been earlier wooden bridges on the site since Norman times, the current road bridge was constructed of cast iron in 1816 during the Regency period, to designs initially by John Rennie, but greatly modified by the John Rastrick

The bridge crosses the river Wye which has one of the highest tidal ranges in the world

27. We’ve now left Wales & are entering England…


When there’s no scaffolding this bank would be a great place to view the length of the Castle from, but we couldn’t get a shot today so focused the camera down river…


28. Ok, the light’s fading so cross back over & turn left along the area known as Riverside passing the rather elaborate bandstand…



It’s a nice part of the town this & it’s hard to imagine it was once a major shipping wharf known as Gunstock Wharf, exporting timber in the 18th & 19th centuries. During the Napoleonic Wars huge amounts of timber was exported from here to build warships

28. The Riverside merges into an area called The Back which is another name for a wharf. If you look across the river you’ll see a hole halfway up the cliff…


Called the Gloucester Hole, this is a natural cave, but it has been enlarged over the years. There’s several stories associated with it, one being that Brunel used it to store explosives in whilst building the railway bridge

29. On the right’s The Riverside Wine Bar…a Tapas Bar



…& then The Boat Inn…


A date in this building suggests that it was built in 1789. The pub retains many of the interior features, such as the low ceiling & stone flags on the floor. At one time the inn was known as the Chepstow Boat. From around the World War II to the 1980s the building was a private home. Inquests were held in the building in the 19th century, often into the deaths of people recovered from the river – charming!

The inn was built alongside a dry dock, where ships’ hulls were repaired until the mid-19th century. Previously it was known as “Hell’s acre” because of the rowdiness & fights were common when sailors hit the bottle in the dozen or so pubs in the area


In 1880, four men who held “respectable positions” in the local community, were tried for hauling a fishmonger called Thomas Scott from the Boat Inn & throwing him into the river on the evening of the Chepstow boat races. The defendants said Scott had reneged on a bet. They were fined 30s each, plus costs & told they were lucky not to be on trial for manslaughter


One area of the Boat Inn, in the section to the right of the entrance, is said to be haunted. A notice painted on the wall advises customers: “While sitting here you [may] experience a sudden shiver or catch a fleeting glimpse of a figure from times past …”

30. Further down the river is the Railway Bridge built by Brunel in 1852 & later modified by British Rail


We can’t get down that far so turn right & follow the road to Lower Church Street…



31. At the T-Junction straight ahead’s the old Fire Station which dates back to 1938…


Turn left up Lower Church Street…



There’s some interesting & impressive sketches on the wall…


32. The road turns into an alley up to the church…


St Mary’s Church, Chepstow has parts that date back to the 11th century in line with the Castle. It was founded around 1072 as a Benedictine priory by William FitzOsbern & his son Roger de Breteuil, 2nd Earl of Hereford.  As Chepstow developed as a market town & port around the castle & priory during the medieval period, the nave became used as the parish church. Accommodation was built on the south side of the church, in the 13th century & the first vicar appointed in 1348



Part of the Norman church remains, but it’s really been changed over later centuries. The main central tower of the original church collapsed in a storm in 1701. The church contains two fonts, one from Norman times & the other from the 15th century

33. With your back to the church turn right & walk down Upper Church Street..


…where we arrive back at the Castle car park where we started this walk

So…that’s Chepstow. In the past we’ve stayed up the hill (in the posh part), but the bottom of the hill’s good too & so much cheaper. It’s a lovely town & the locals are really friendly so…

Go Walk!