Town Trail

Three walking trails are designed to lead you on interesting routes around the town mainly within the old town Portwall. The most popular route is the Town Centre Trail, whilst the one most suited to the less energetic is the Riverside Trail. All routes start and finish at the Castle Car Park and the time taken to cover them is a matter for the individual, but as a guide the full route which starts off with an amble up the Castle Dell, alongside the Castle, takes approx. 90 minutes.

Town Centre Trail: From the Castle Car Park/Tourist Information Centre turn right up

  1. Bridge Street. It is best to cross the road taking care due to restricted vision up the road. The first places you pass by are the Stuart Crystal workshops and historic Cromwell House the home of Riverside Pottery and Gallery, both worth a visit on your return. Note also that there is a quiet and almost hidden little public garden a little way up from Riverside Pottery and Gallery. The garden is a feature that involved a lot of local effort to realise a design by local landscape gardener Stella Caws. On the way up the street you will see on the right an impressive terrace of fifteen bow windowed houses, which give the street, its character and which were built between 1805 and 1823. At the top of the street on the right is:
  2. Powis Almshouses. Built in 1721 these almshouses had rooms for 6 men downstairs and for 6 women upstairs. Thomas Powis who was born in the town but prospered as a vintner in Enfield provided them. Leading off Bridge Street to the left is
  3. Upper Church Street. Where on the left you will see Davis Court, a sheltered housing unit for the elderly - perhaps the modern equivalent of the old almshouses. Adjacent you will see:
  4. Montague Almshouses. Provided in the will of Sir Walter Montague who died in 1615. They originally housed 5 men and 5 women, but the property was rebuilt after the Second World War, preserving part of the original facade. The neighbouring houses dating from the 18th century should also be noted. Opposite the almshouses run up:
  5. St. Mary Street. Pedestrianisation of this street in 1991 has given this popular shopping and commercial street a new lease of life and the shops along the street and in St. Mary's Arcade, which leads off it, are worth time to explore. Those interested in architecture will note a wide variety of styles above the shop fronts. At the top of St. Mary Street is the town map. A work of art commissioned for the town by the Chepstow Chamber of Commerce & Enterprise and painted by Keith Underwood, a well-known local artist. Continue into:
  6. The High Street. This has always been the main shopping street of the town and whilst a lot of the development of the recent past has removed much of the character that the street once had, interesting features remain. One prominent feature along the street is Herbert Lewis's "Coronation Buildings" built by the family business that continues as "The Chepstow Department Store". Just before this you pass the entrance to a small lane, Oxford Street, an interesting example of the many small streets which lay behind the main streets in the 19th century. Note the stone sets adjacent to the walls of the buildings on either side. Now becoming rare these were once commonly provided to protect buildings from damage due to being struck by protruding wagon wheel hubs. At the top of the street on the right is an interesting group of buildings forming White Lion Square, an area once known as "Pye Corner" with the pub being called "The House at Pye Corner". If you now look down the street you will see the cliffs above the River Wye. This end of the High Street is dominated by:
  7. The Town Gate. Originally built in the late 13th century at the same time as the Portwall, the Town Gate has been subject to rebuilding and restoration over the years. The archway once had a gate, portcullis and guardroom, and was used as a collection point for tolls. All cattle and goods taken through the gate to be sold were liable to market dues payable to the Lord of the Manor. Collection of tolls continued into the 19th century. Next to the Town Gate is:
  8. The Gatehouse. An inscription carved in the wooden doorframe "A.N.D.1609 M.C." commemorates an early rebuilding of the Gatehouse by a wealthy widow Mrs Margaret Cleyton. On the wall of the building you will see a plaque hung by the Chepstow Society to pay tribute to the memory of Mrs Cleyton, whose generosity was to the considerable benefit of the town. This building has subsequently undergone several major internal and external alterations. Behind the Gatehouse is the Place de Cormeilles, named after the town in Normandy with which Chepstow is twinned. The connection dating back to 1067 - The pleasant little square was refurbished in 1991 and now offers an agreeable place to rest awhile and take a close look at the Portwall, which runs alongside.
    From here either take a walk through the Town Arch and up Moor Street and back, where you see the fine old Police Station which was recently used as a television film set, or cross over the High Street into White Lion Square and walk downhill a little way along Bank Street. Walk to your left through the new Manor Way shopping development and past the new library to:
  9. The Portwall. This stretch of the town wall, which now encloses the main car park, leads down to a fine view over the castle and castle dell. Retrace your steps back to Bank Street or use one of the other routes out of the car park towards the town centre. Turn left, downhill towards:
  10. Beaufort Square. Originally this was just "The Square" and was the centre of life in Chepstow. Before modifications to cater for modern traffic the square was a gentle sloping open space where fairs, markets, celebrations and election rallies were held.
    Once children danced around the maypole here. A whipping post and pillory also stood here. Across the square notice the Beaufort Hotel which in bygone days was the coaching inn for the town. There are some buildings around the square, which date back to the 18th and early 19th centuries. The TSB building which is new but nearly replicates the facade of the 1807 market house and assembly rooms. The British Legion building is unusual locally in that it has a Regency iron canopy and bow window. Further down is a house named "St. Maur", where Nelson once stayed. At that time the house was the Three Cranes Inn and was one of as many as 75 public houses in the town.
    The War Memorial, recently enclosed by iron railings;donated to the town by the Army Apprentice College before it closed, is prominent in the square and next to it you will see the gun from a captured German First World War submarine. King George V presented it to the town in recognition of the gallantry of Able Seaman Williains V.C, a Chepstow man killed during the landings at Gallipoli. Although mortally wounded, he continued to hold small boats in place for over an hour, forming a bridge to the shore from the landing ships. Able Seaman Williams was posthumously awarded the Victoria Cross for this action. Leave the square by taking the road to the left of the National Westminster Bank known as:
  11. Hocker Hill Street. This picturesque steep old cobbled street displays a variety of 18th and 19th century buildings. Interesting examples of bow windows and door frames are to be found. At the bottom on the left is the Five Alls Inn noted for its unusual inn sign. At the corner of the road is an arched doorway to a former wine cellar below the Powis Almshouses, evidence of the once thriving wine trade in Chepstow. From here it is a short walk back down Bridge Street to your start point or you can continue your exploration of the town by following the Riverside Trail in reverse starting from item 19 - St. Mary's Church to be found at the end of Upper Church Street.

    Riverside Trail: From the Castle Car Park/Tourist Information Centre cross Bridge Street and see-
  12. The Museum. Situated in Gwy House, an elegant late 18th century town house. The museum is well worth visiting. Once the home of prosperous merchant families it has since been used as a school and as a hospital, prior to being adapted for use as a museum. The museum collections reflect the history and development of Chepstow and the surrounding area. (See p 1 8) Carry on towards the river and on your left you will pass the award winning Afon Gwy Restaurant. Almost opposite is;
  13. St. Ann Street. Your walk is straight on, but a little detour into the street will provide you with a view of some picturesque 17th and 18th century cottages. Beyond St. Arm Street on the right is;
  14. The Bridge Inn. This recently refurbished premises is, one of the surviving public houses out of a total of the 75 that were in business in the town 100 years ago. At one time this well-known watering hole was known as The Ship Inn.
  15. The Old Wye Bridge. (Now floodlight on summer evenings.) Until January 1988 the main-road bridge into the town from Gloucestershire. This fine cast iron structure is now a protected monument and restricted to light traffic only. The bridge as you see it today was built in 1816 by John Rastrick of Bridgenorth, but increasing traffic volume and weight required that it be strengthened several times prior to the building of a new bridge downstream.
    The bridge is at least the sixth to be built on this site and prior to use of this site as a crossing the Romans had a bridge about half a mile upstream. The early wooden bridges lasted 30-50 years before the need for major repairs or replacement and it is known that the bridge was purposely destroyed during the Civil Wars.
    Maintenance of the bridge is made difficult by the extraordinarily high rise and fall of the tide. At 40 feet (12m) range, the rise and fall of the tide is second only to that in the Bay of Fundy in Nova Scotia where the range averages 46 feet (14m). The centre of the bridge marks the boundary between England and Wales; thus you can stand with one foot in each country. (Watch the traffic whilst taking photos!) The centre panel of the bridge parapet marks the spot, indicating the divide between Gloucester and Monmouth. (A detour and climb to the top of the cliffs opposite will reward you with fine panoramic views of the town and beyond.) Retrace your steps and rum left along the riverbank to see the;
  16.  Riverside and Port Area. Now a restful riverside amenity area, the part that you now see was once the very busy part of the town. It is not hard to imagine the noise and bustle that would have been normal in the last century when the area was known as Gunstock Wharf. At that time piles of timber were stacked on the foreshore where a row of seats now stand. Behind the timber stood stone built bark houses for the storage of oak bark for tanning - the main export during the 18th & 19th centuries. In times gone by wharves, timber yards, shipyards and brickyards extended from this point all the way downstream to the Hardwick Cliffs. During the time of the Napoleonic wars vast quantities of timber was exported for building warships in navel shipyards. At this time wooden merchant ships were built at three shipyards in Chepstow. A plaque on the wall of the Wye Knot Restaurant on your right records the embarkation of the leaders of the Chartist uprising, to start the sentence that they should be "transported" to Van Diemen's Land, now known as Tasmania. The road you are on is known by the unusual name of: 
  17. The Back. A curious name meaning a wharf. (Bristol has its Welsh Back). Look across the river and you will see what appears to be a cave half way up the cliff face. This is "Gloucester Hole" a natural cave, but the hole as it is today has been excavated into the cliff face by man. Legend has it that Brunel used the hole as a store for explosives during the building of the Railway Bridge. At other times it is reputed to have been used as a tea warehouse. The Union Jack painted on the rockface has been there since at least 1935 and is regularly repainted.
    On your left on the nearside bank of the river you will see modern work designed to improve the area for visitors, this includes the restored former "Packet Slip" which was latterly used by the salmon fisheries as a slipway for their boats. To the landward from here stood the offices of the Wye Fisheries until 1986. Salmon was, as you may expect, the usual catch. How many fishing tales have been told at The Boat Inn on your right?
    Today there is no remaining evidence of the dry dock that was once a prominent riverside feature. You walk over the site of the dry-dock as you approach the Boat Inn. The dock was opened in 1759 for ships up to 500 tons. The dock gates broke in the mid 19th century and were never repaired. Silting up followed and soon the site was used as a rubbish tip. Once filled and levelled the site became the venue for Travelling Theatres etc.
    It is from here that a market boat to Bristol departed during the 17th & 18th centuries. As early as 1822 a steamboat replaced the earlier sailing craft. The pontoon that stands was designed and installed by The Chepstow Boat Club in 1998 and provides a landing point for river craft and canoeists. It is designed to encourage a revival of interest in the river Wye for river cruising.
    Adjacent to the Boat Inn stands the modern Riverside Mill apartment block occupying a site which includes a large stone warehouse dating from around 1790. The façade is retained as a prominent feature. From the late 16th century various buildings in this area were used as customs houses until 1882 when Chepstow ceased to have its own customs officers.
    Whilst in this area you may notice precautions taken to prevent ultra high tides from entering premises.
    In the spring of 1996 nearly 10,000 sandbags were issued in Chepstow and Tintern as a precaution against the highest tides and the area looked as though it were a war zone. Downstream you will see the modern Road Bridge opened in 1988 to carry the main road to Gloucester. Beyond it and obscured by the new bridge is Brunel's Railway Bridge opened in 1852 and considerably modified by British Rail in 1962. The road leading up from the river and towards the town is:
  18. Lower Church Street. As you join the street you will see the Dendix Brush factory on your left and on your right a Fire Station dated 1938 and now the home of Derek's Gym. If you walk across the car park beyond this building you will come to the Drill Hall which has recently been extensively refurbished and enlarged tolact as an "Educational Resource Centre" providing a place for school parties to study the history and geography of Chepstow and the surrounding area.
    Returning to the street you will see the apparently small Workshop Gallery. A pottery workshop and gallery of renown and well worth a visit. The rows of houses in this street are typical of working class Chepstow in the 19th century. Note Kendall Square on your left, a "restored" and well-hidden courtyard of 8 small houses. Further up the street beyond the sharp right and left turns and on the right opposite the church is the quaint old Howells Row. The new development alongside is Hollins Close, which demonstrates a close harmony between old and new architecture. On the left at the top of the street is the main entrance to:
  19. St. Mary's Church. Directly in front of you as you leave the church is
  20. Upper Church Street. At the far end of this street you come to -
  21. Bridge Street. Towards the bottom of the street beyond the Three Tuns Inn is the Castle Car Park/Tourist Information Centre the starting point of your walk.

    Full Town Trail: You have the choice of walking the Town Centre Trail followed by the Riverside Trail or this alternative route:

    From the Castle Car Park/Tourist Information Centre face the castle and take the well-used and recently improved footpath that passes alongside the castle. (Until recently you would pass by an area of corrugated iron fencing which was in place for over ten years as a safeguard during essential maintenance work.) The area that you will walk through to reach Welsh Street at the upper end of the High Street is known as;
  22. Castle Dell. The Castle Dell was opened to the public with great ceremony in 1886 when the Duke of Beaufort leased it to the town for one shilling a year. The four sided stone seat half way up was erected for Queen Victoria's Jubilee, and the drinking fountain at the top originally stood just off the High Street. From the Dell you get good views of the castle and of part of the Portwall, which is above you on the left, as you proceed. Leaving the Dell through wrought iron gates brings you into;
  23. Welsh Street. Turn left and walk towards the traffic lights ahead of you, on your way look out for a set of horse mounting steps on the opposite side of the road standing by a tree and which once served practical use in the town centre. The steps are very near to the popular CAMRA Real Ale Award winning pub - The Coach & Horses. Across the road at the junction is the George Hotel, to the left is the High Street and to the right is Moor Street, where you will find easily missed shopping opportunities. At the traffic lights you join the Town Centre Trail at item 7. - The Town Gate.

    When you reach the bottom of Hocker Hill Street (11.), continue down Bridge Street noting items 1. and 2. Once you reach the Castle Car Park/Tourist Information Centre you begin the Riverside Trail