A guide to the points of interest of Y Sir Fynwy


The route of Y 100 Sir Fynwy provides a magnificent tour around the historic county of Monmouthshire – an area that corresponds to the present-day local authorities of Monmouthshire, Blaenau Gwent, Newport and Torfaen, as well as the parts of Caerphilly and Cardiff that lie east of the Rhymney River.

The territory that became Monmouthshire was once part of the early Welsh kingdoms of Gwent and Glywysing and, after the Norman conquest, of the Welsh Marches. It became one of thirteen historic Welsh counties in 1535 under the Laws in Wales Act. This Act abolished the marcher lordships that had long been a feature of the border region with England and that were closely associated with its many castles, several of which lie on or near our route.

Monmouthshire's Welsh status was somewhat ambiguous between from the mid-16th to the latter part of the 20th centuries. Some considered it to be part of England during this time, while there were often references to “Wales and Monmouthshire”. Its legal inclusion in Wales was finally clarified by the Local Government Act 1972.

Whatever the legislative ambiguities, what is beyond dispute is that the Y 100 Sir Fynwy route offers spectacular natural scenery from seascapes to hills and valleys, as well as majestic examples of the built environment encompassing abbeys, castles and churches that have long inspired artists, poets and even prominent Nazis!

Section 1 – Chepstow to Rogiet

Chepstow – the headquarters of Y 100 Sir Fynwy can trace its origins back to Mesolithic and Roman times, with today's settlement rising in prominence after the Norman conquest when its location next to the Rivers Wye and Severn made it a key base for control of the Welsh Marches. The magnificent Chepstow Castle is believed to be the oldest surviving post-Roman stone fortification in Britain and has kept a watchful eye over the town from its cliff top vantage point since 1067. A noted port in the Middle Ages, the town became a focal point of early British tourism (the Wye Tour), while shipbuilding, heavy engineering and horse racing have also played important roles in the town’s development. (A – ST 527945)

Wales Coast Path – Chepstow is one of the termini of the Wales Coast Path. Opened in 2012, the 870 mile route is currently the only continuous path around a country’s entire coast line – England is currently trying to catch-up! (B – ST535930)

Bulwarks camp - this small hill fort on top of cliffs overlooking the River Wye and the Severn estuary is thought to have built in either the first century BC or the first century AD. The Romans called the inhabitants of the area the Silures. Like the South Wales LDWA that has followed them, the Silures are described as “…a powerful and warlike tribe”. (C - ST 534925)

The (Old) Severn Bridge – replacing a ferry crossing when it opened in 1966, the suspension bridge has become a local icon and is Grade I listed. The bridge is actually comprised of four structures (the Wye Bridge, Beachley Viaduct, Severn Bridge and Aust Viaduct). It crosses the Rivers Wye and Severn via Beachley peninsula, home to an army barracks, on its way to Aust in South Gloucestershire. Unlike its more recent sibling, the bridge has pedestrian and cycling access that provides a popular recreational route between Wales and England. Tolls used to repay the financing of the bridge were removed in December 2018 – no longer would Welsh poet Harri Webb’s words Ode on the Severn Bridge have quite the same resonance

Two lands at last connected
Across the waters wide
And all the tolls collected
On the English side

(D – ST537914)

Mathern -  an historic settlement on the outskirts of Chepstow, Mathern is associated with St Tewdrig. A former king of Gwent, Tewdrig is said to have been mortally wounded at Tintern around 630 AD before succumbing to his wounds at what is now Mathern. It is also home to Grade I listed Mathern Palace, formerly the main residence of the Bishops of Llandaff but now in private hands. (E – ST524910)

Marriott St Pierre Golf and Country Club – incorporating a former 14th century manor house and deer park, as well as the Grade II listed Church of St Peter, this branch of the famous American hotel chain is home to a championship golf course that has hosted a number of prestigious tournaments including the British Masters and Solheim Cup.  (F – ST520904)

St Pierre Pill – now the home base of the Chepstow and District Yacht Club, this small harbour was once a much grander affair. A medieval manuscript refers to it as "one of the three great ports of Britain”, while as recently as 1860 barges of up to 70 tonnes could travel as far upstream as today’s golf club. The small lighthouse is known as Redcliffe Lights.

(G – ST519896)

Black Rock – an important crossing point of the River Severn for many centuries, Black Rock is today known as a bastion of the traditional method of fishing for salmon with ‘lave nets’. These Y-shaped willow framed nets are deployed by hand at low tide. The Black Rock fishermen, who promote the fishery as a heritage site, have their own names for areas within the fishing grounds such as Monkey Tump, Lighthouse Vear and The Grandstand. (H – ST512881)

Sudbrook & Sudbrook Pumping Station– the village of Sudbrook was built in the late 19th century to house workers building the nearby Severn railway tunnel. At more than four miles in length, the Severn Tunnel was the longest mainline rail tunnel in Britain from its opening in 1886 until the arrival of the Channel Tunnel (HS1). Its construction was a major feat of engineering whose challenges included contending with a major underground freshwater river, known as the Great Spring, that led to the pioneering use of scuba gear. Sudbrook Pumping Station continues to remove millions of gallons of water each day from the tunnel, with its output having found a variety of uses including at the Magor Brewery, the Ministry of Defence and formerly a paper mill (closed 2006). (I – ST506874)

Second Severn Crossing – opened in 1996, and officially renamed the Prince of Wales Bridge in 2018, the cable-stayed bridge marks the lower limit of the River Severn and the start of the Severn Estuary.

J – ST492872)

Caldicot Level / Gwent Levels – a low-lying area of wetland and tidal mudflats, the Caldicot Level stretches between the Rivers Wye and Usk covering 17,500 acres (71 km2). Together with the Wentloog Level on the Eastern side of the Usk, it forms the Gwent (or Monmouthshire) Levels. Formed from river and tidal deposits, the levels have been repeatedly inundated and reclaimed from the Severn Estuary by humans since Roman times. The levels are very rich archaeologically, with finds from the Mesolithic, Bronze Age and Iron Age periods, while also being an important wetland resource. Parts are designated as Sites of Special Scientific Interest and they are registered as a Historic Landscape of Outstanding Historic Interest in Wales. The Levels are criss-crossed by drainage channels, known locally as 'reens’, a couple of which are crossed on Y 100 Sir Fynwy. (K – ST483871)

Section 2 – Rogiet to Foresters Oaks Car Park.

Severn Tunnel Junction / Rogiet – now primarily a commuter station for Cardiff and Bristol workers, STJ has a rich railway history. The meeting point of the South Wales Main Line to London and the Gloucester-Newport Line, until the 1980s it was a major marshalling yard and depot for coal going out to England and other goods coming into Wales. It was also the terminus of a car transport service through the tunnel until the opening of the Severn Bridge. The surrounding village of Rogiet grew up with the railway but is now largely a dormitory village. (L –ST461879)

The Monmouthshire Way – The close (and slightly older) relative of Y 100 Sir Fynwy, the Monmouthshire Way is a circular long-distance footpath of 121 miles that explores the historic county of Monmouthshire with short excursions into a few of its neighbouring counties. It was designed by LDWA Chair, Dave Morgan. (M – ST444916)

Llanfair Discoed –Mentioned in the Domesday book of 1086 as ‘Lamecare’, the village’s name loosely translates to ‘Mary’s church under the wood’. It is home to a small ruined castle, believed to have been built by the FitzPayn family in the 13th century. (N – ST447923)

Gray Hill – With commanding views across to the Severn Estuary and Gwent levels, Gray Hill boasts prehistoric standing stones and a stone circle. Dated to the Bronze Age, little is known about the original purpose of the stone circle although astronomical alignments have been suggested. (O – ST434935)

Wentwood Reservoir – Visible from Gray Hill, the reservoir was opened in 1904 to supply water to south east Gwent. It is currently being brought back into service, with its use more recently having been restricted to recreation and fishing. These works led to a grisly discovery in 2017 when the remains of Sandie Bowen, murdered by her husband in 1997, were discovered.  (P – ST430932)

Section 3 – Foresters Oaks Car Park to Usk.

Wentwood / Foresters Oaks – the largest ancient woodland in Wales, Wentwood has a rich history. The forest originally stretched between the rivers Usk and Wye dividing Gwent into two – Gwent Uwchcoed and Iscoed (above and below the wood). A Royal Forest in the Middle Ages, it once had its own laws with court sessions held at Forester's Oaks – the guilty could even be hanged, a practice that continued until 1829. Welsh Oak from the forest has been used for Royal Navy battleships in the Napoleonic era, although the native timbers were largely used for charcoal to support the local iron industry. Most of the native trees were felled in WWI for use in the trenches. Originally replaced by conifers, more recently broadleaf species have been re-introduced bringing it ‘Queen’s Commonwealth Canopy’ status in recognition of its increasingly important wildlife and conservation role. (Q – ST429939)

Usk Valley Walk – a long distance footpath stretching 48 miles from Caerleon, a town located on the site of the former Roman legionary fortress of Isca Augusta, to Brecon. (R - ST396941)

River Usk – rising on the northern slopes of the Black Mountain in the western part of the Brecon Beacons National Park, the River Usk flows for 63 miles to reach the heart of the city of Newport and then empty into the Severn estuary at Uskmouth. Designated a Site of Special Scientific Interest, the Usk is a noted salmon and trout fishing river. An important historic trade route, the Usk also features prominently in folklore including the tales of King Arthur. (S – ST387944)

Bertholey House – with wonderful views over the River Usk, this mansion house has had an eventful life. With 16th-century origins, it was remodelled in the late-18th- and early-19th-century, before being burnt down to a derelict shell in 1905 – a mishap attributed to a drunken relative of the owner. It was finally restored in 1999 and is now the headquarters of property development firm The Bird Group.

(T – ST397945)

Section 4 – Usk to The Bryn

Usk – with a rich history dating back to Roman times, the small town (pop: 2800) of Usk is today known as the ‘town of flowers’ having won a Gold Award in the RHS Britain in Bloom 36 times since 1981. It has a steelier side to its character, though, as it is also home to HM Prison Usk. (U - SO378004)

Llancayo windmill – Clearly visible across the River Usk (albeit 0.5 mild distant), Llacayo windmill dates back to 1813, grinding wheat until 1830 when it fell victim to a fire.  It stood in ruins until 2006 when a three-year restoration project began to turn it into today’s self-catering accommodation set across five floors.  

(V – SO365031)

Trostrey Lodge -  a late Georgian country house, the Grade II listed building was previously part of the Trostrey Court estate with an associated mill and iron forge. It is believed to have been rebuilt as a private school in the earlier 19th century. (W – SO356074)

Clytha Park – the route passes just to the west of Clytha Park estate, home to what is regarded as one of the finest neo-classical houses in Wales. Owned by the National Trust, the Grade I listed house remains the private residence of the Hanbury-Tenison family and is accessible only by prior appointment. The wider estate features two other prominent architectural features, namely the Grade II* listed gates to the park and the Grade 1 listed folly Clytha Castle. (X – SO363089)

Pant-y-Goitre Bridge - crossing the River Usk between Abergavenny and Usk near the village of Llanfair Kilgeddin, this Grade II* listed bridge was designed and built in 1821 by John Upton as part of the improvements to the Abergavenny to Usk turnpike road.  Constructed of Old Red Sandstone, the bridge has three spans and is described by architectural historian John Newman as, "an unusual and handsome design". (Y – SO348090)

Section 5 – The Bryn to Abergavenny

The Bryn – a small hamlet about three miles from Abergavenny, it is home to Grade II* listed St Cadoc’s Church which dates back to the 15th century. The village is also home to the The Bryn Trading Post community shop.  (Z - SO331097)

Penpergwm Lodge – a B&B on the outskirts of the eponymous village, it is noted for its garden. Based on the original Edwardian layout, it features open lawns, some formal areas, hedges and, and terraces, as well as a folly pre-war kitchen garden. (A1 – SO335103)

Section 6 – Abergavenny to Cwmyoy

Abergavenny – a market town with a population of around 12,500, Abergavenny sits at the confluence of the River Usk and its tributary stream, the Gavenny. Its name translates to "Mouth of the River Gavenny”, with the latter derived from a Celtic word Gobannia meaning "river of the blacksmiths", indicating the town's pre-Roman importance in iron smelting. Abergavenny is surrounded by mountains and hills, most notably its ‘three peaks’: the Blorenge (1834 ft), the Sugar Loaf (1955 ft), and Ysgyryd Fawr / The Skirrid (1594ft).  Originally the site of a Roman fort, Gobannium, Abergavenny became a medieval walled town within the Welsh Marches and contains the remains of a medieval stone castle built soon after the Norman conquest of Wales. (B1 – SO300146)

The Black Mountains - the easternmost of the four ranges of hills that comprise the Brecon Beacons National Park, the Black Mountains are roughly defined by a triangle formed by the towns of Abergavenny (south) and Hay-on-Wye (north) and the village of Llangorse (west). Its ease of access and fine views make it very popular with walkers. Its highest peak is Waun Fach (2,661 ft). (C1 – SO292175)

Sugar Loaf – the southernmost of the summit peaks (1 955 ft) of the Black Mountains. Like other hills of the same moniker, it takes its name from its perceived resemblance to the sugarloaves which were the usual form that refined sugar was sold in until the late 19th century. Often erroneously thought to be an extinct volcano due to its conical shape, it is in fact composed entirely of sedimentary rocks. The Sugar Loaf is one of three locations thought be the inspiration for the hymn “All Things Bright and Beautiful". The mountain is owned by the National Trust.  

(D1 - SO272187)

Brecon Beacons National Park – one of three National Parks in Wales, the Brecon Beacons NP covers 519 square miles  and stretches from Llandeilo in the west to Hay-on-Wye in the northeast and Pontypool in the southeast. Most of the park is moorland with scattered forestry plantations, while it is also known for its waterfalls and remote reservoirs. Due to the relative remoteness and harsh weather of some of its uplands, the park is used for military training with UK Special Forces holding demanding selection training exercises within its boundaries – the SAS’s ‘Fan Dance’ being the best known. The entire national park was designated an International Dark Sky Reserve in 2013. (E1 - SO272187)

Section 7 – Cwmyoy to Llanthony

Cwmyoy / Cwmyoy Church – the hamlet of Cwmyoy is best known for St Martin's Church, described as the "most crooked church in Great Britain." Dating from the 12th century the Grade I listed church ’s extreme tilt is the result of a landslide and has been subject to several efforts to prevent its collapse including the use of buttresses and tie beams. Inside the church there is a fine stone cross dating to the 11th or 12th century believed to have once stood in the churchyard to be venerated by pilgrims travelling through the Black Mountains to St David’s Cathedral in Pembrokeshire.

(F1 - SO301226)

Vale of Ewyas - the steep-sided and secluded valley of the River Honddu, it is named after a small Welsh kingdom thought to have existed in the area following the Roman withdrawal from Britain. (G1 – SO295253)

Section 8 – Llanthony to Longtown

Llanthony / Llanthony Priory – the village of Llanthony is dominated by its partly ruined former Augustinian priory that dates back to around 1100 when it was built by the Norman nobleman Walter de Lacy on the site of an existing chapel. Regularly raided by the Welsh and seemingly little used, it was merged in 1481 with its daughter monastery at Gloucester before being suppressed by Henry VIII's Dissolution of the Monasteries. Within the precincts of the Priory there are three other buildings that also have Grade I listed status: the Abbey Hotel, St David's Church,] and Court Farm Barn. The ruins have regularly attracted artists, including J. M. W. Turner who painted them from the opposite hillside.

(H1 - SO288276)

Beacons Way – crossing Y 100 Sir Fynwy route at Llanthony is the long-distance footpath, the Beacons Way. The 95-mile linear route traverses the Brecons Beacon National Park from Abergavenny in the east to Llangadog in the west. (I1 – SO308270)

Hatterall Ridge – this 10-mile ridge in the Black Mountains carries the border between Wales and England along its length, as well as Offa’s Dyke Path. The western side of the ridge is the limit of the Brecon Beacons National Park.

(J1 - SO308270)

Offa’s Dyke Path - one of Britain's official ‘National Trails’, Offa’s Dyke Path is a 177-mile long distance from the Severn Estuary at Sedbury, near Chepstow, to Prestatyn on Wales’ north coast. The route is named after and closely follows, Offa's Dyke, an earthwork constructed in the 8th century on the orders of King Offa of Mercia. (K1 - SO308270)

Section 9 – Longtown to Pandy

Longtown – with Y 100 Sir Fynwy route now in England (Herefordshire), the village of Longtown was named because the settlement is strung out along the lowland / winter road that connects Hay-on-Wye with Abergavenny. Established as a Norman colony, Longtown retains the ruins of its original 11th century motte and bailey castle.  (L1 - SO322290)

Walterstone – the small village of Walterstone is home to a motte-and-bailey castle and the Grade II-listed St Mary's church. (M1 – SO339251)

River Monnow – marking the Wales-England border for much of its 42 miles, the Monnow rises near Craswall just below the Black Mountains. Picking up various tributaries crossed during Y 100 Sir Fynwy (Olchon Brook and River Honddu), it flows southwards to Monmouth where it joins the River Wye. The unique medieval Monnow Bridge in Monmouth is the only remaining fortified river bridge in Great Britain with its gate tower standing on the bridge. The Monnow is a noted fishing river, particularly for brown trout. The 40 mile long-distance Monnow Valley Walk follows the river. (N1 – SO335233)

Section 10 – Pandy to Treadam

Pandy – named after the Welsh word for fulling mill, a stage in woollen cloth making, the village of Pandy served the Llanover estate for this purpose in the 17th century. (O1 - SO332214)

Llangattock Lingoed – this small village is home to two notable buildings, the Old Court and St Cadoc’s church. The former is a Grade II* listed medieval hall house dating from the late 15th century, while the latter is Grade I listed medieval structure noted for its interior that a large wall painting depicting St George slaying the dragon – one interpretation of the painting is that it is a reference to the defeat of Owain Glyndŵr by the English at the battles of Campston Hill (1404) and Grosmont (1405), which were fought nearby.  (P1 - SO361200)

White Castle – with its powerful drum towers, expansive walls and moat, White Castle presents an imposing site in a very rural part of Monmouthshire. It likely takes its name from the white rendering applied to its external walls, although an alternative explanation is that it stems from the name of a local ruler of early Norman times, Gwyn ap Gwaethfoed (Gwyn being the Welsh for White). During World War II, White Castle was painted by Adolf Hitler’s deputy Rudolf Hess.  A prisoner of war at Maindiff Court Hospital near Abergavenny, Hess is reported to have been regularly taken to the castle to paint, sketch and feed the swans in the moat. (Q1 – SO380166)

Three Castles Walk – a 20 mile route with fine views of the Welsh Marches, the Three Castles Walk connects the triumvirate of fortifications – White, Grosmont and Skenfrith  - that defended the area from Welsh attacks soon after the Norman conquest. All three began life as earthworks with wooden buildings, before being rebuilt into more substantial defensive structures. Their collective moniker denotes the fact they were brought under the control of a single lord, Hubert de Burgh, at the turn of the 13th century. Later in the 13th century, the three castles were given to future King Edward II and then to his younger brother, passing into use as royal homes and administrative centres. By 1538, however, all three were abandoned and in ruins. (R1 - SO380166)

Section 11 – Treadam to Monmouth

Treadam Barn - a restored 15th century oak-framed barn situated on the Offa's Dyke path between Monmouth and Abergavenny. It now caters for B&B, holiday lets and events. (S1 - SO380156)

Llantilio Crossenny – this small village is said to be on the site of a 6th century battle between King Ynyr of Gwent and the Saxons, with legend holding that the King successfully prayed to St Teilo to help him defeat his enemy. Accordingly, the village’s noted Grade I listed church is named in tribute to their benevolent saint. (T1 – SO397147)

Llanfihangel Ystum Llewern – named to trip up the tongues of visiting English walkers, this small village is located close by the River Trothy which joins the River Wye just south of Monmouth. (U1 – SO433139)

Section 12 – Monmouth to Redbrook

Monmouth - the county town of Monmouthshire since 1536, Monmouth is situated at the meeting point of the Rivers Wye and Monnow (from which its name is derived). The town was the site of a small Roman fort, Blestium, before becoming more established after the Normans built a castle here after 1067. Its medieval stone gated bridge (Monnow Bridge) is the only one of its type remaining in Britain. Monmouth Castle was the birthplace of King Henry V in 1387, while other famous names associated with the town are Geoffrey of Monmouth and Charles Rolls – the former a seminal 11th century historian widely credited as shaping the myths of King Arthur, and the latter a motoring and aviation pioneer who co-founded Rolls Royce and was the first Briton to be killed in a powered aircraft accident.  With a population of c10,500, today Monmouth is primarily a shopping, services and education centre. Monmouth School, the Y 100 Sir Fynwy checkpoint, was founded in 1614 and is run as a trust by the Worshipful Company of Haberdashers, one of the livery companies. (V1 - SO512126)

Kymin - with extensive views of Monmouth and beyond, the Kymin has long welcomed visitors to its summit. Once part of the large Monmouthshire estate of the Duke of Beaufort, it was already a popular picnic site in the late 18th century. The Kymin features two notable buildings. The charming Round House stands proudly atop the hill, built in 1794-6 with subscriptions from the Monmouth Picnic Club (Kymin Club) to provide "security from the inclemency of the weather". The Kymin is also home to the unusual Naval Temple, built from money raised by the Kymin Club and public subscription in 1800, it celebrates some of the greatest British admirals and victories of the time. (W1 – SO528125)

Section 13 – Redbrook to Trellech

Redbrook –  back in England, now in Gloucestershire, the unassuming village of Redbrook boasts a proud and extensive industrial heritage. Its past endeavours encompass not only corn and paper mills, but also copper, iron and tinplate works. Initially dominated (17th century) by copper production, it later became world renown for its tinplate, which continued to be produced in the village until 1962.  Redbrook takes its name from its industrial past, with the use of iron ore resulting in the brook running down the valley through the village often running dark red. Still a good place for a beer, with The Bell Inn regularly hosting the South Wales LDWA Christmas party, the village was once home to 13 pubs and three breweries. (X1 - SO537099)

River Wye - the fifth-longest river in the UK, the River Wye stretches 134 miles from its source on Plynlimon in mid Wales to the Severn estuary. For much of its length the river forms part of the border between England and Wales. (Y1 – SO536099)

Penallt Viaduct (Redbrook Railway Bridge) – a monument to the former Wye Valley Railway that ran from Chepstow to Monmouth, the Penallt viaduct stretches more than 300 feet to connect Wales with England.  The Grade II listed iron bridge used to carry a single-track on its five girder spans, but while that is no longer the case it still provides pedestrian access (including to Y 100 Sir Fynwy participants and patrons of The Boat Inn) on a footpath attached to its upstream girders. Plans to restore the bridge have been drawn up by the Wye Valley AONB and local campaigners, but with a price tag of between £600-£900k it has so far been unable to attract the required funding.  (Z1 - SO536099)

Wye Valley Walk – a 136-mile long distance footpath tracing the Wye from the river’s mouth in Chepstow to its source in the Cambrian Mountains in mid-Wales. (A2 – SO534088)

Whitebrook – Hundredeers wishing for a change of cuisine after 80 miles of checkpoint fare have the unlikely option of Michelin starred cooking in the small village of Whitebrook (n.b. advanced bookings and change of clothing advisable). Current chef and owner of The Whitebrook, Chris Harrod, is a renown forager (anyone for charlock, hedge bedstraw or pennywort?) and Welsh winner of BBC’s Great British Menu. The village itself, like the Angiddy valley at Tintern a few miles to the south, was an active industrial centre between the 17th and 19th centuries utilising water power from the steep-sided valley. A branch of the Tintern wireworks was established here in the early 17th century with wire remaining the main industry until well into the 18th century when paper mills assumed prominence in response to growing demands for wallpaper. (B2 – SO534065)

Wye AONB – The Wye Valley Area of Outstanding Natural Beauty covers 126 square miles from just south of Hereford to Chepstow. It straddles the Wales-England boarder including parts of the counties of Gloucestershire and Herefordshire, as well as Monmouthshire, and is noted for its limestone gorges and native woodlands. Ross-on-Wye is the only town within the AONB itself, but Hereford, Monmouth, Coleford and Chepstow lie just outside its boundaries. The AONB is important for wildlife and is home to a number of designated sites, including nature reserves, Sites of Special Scientific Interest (SSSI) and Special Areas of Conservation. (C2 - SO534065)

The Narth – now largely a commuter village, The Narth began life in the 19th century as a settlement to house workers for the paper mills in Whitebrook. Further expansion came in the 1920s when the local land owner, the Marquis of Worcester, sold some his holdings for development. A final phase of development came with the building of council houses in the 1950s. The origin of the village’s unusual name remains unclear. A derivation of the Welsh word for a clearing “narth”, as well as a corruption of north have both been suggested, but it is thought that it most likely comes from “garth”, Welsh for enclosure, hill or ridge. (D2 – SO521064)

Section 14 – Trellech to Tintern

Trellech – now a small village, back in the 13th century Trelleck was one of the largest towns in Wales. It is believed that its prominence at that time reflected its proximity to iron ore from the Forest of Dean and charcoal from the surrounding woodlands, enabling it to produce weapons, armour and other military goods for the military activities in Wales. Harder times were to follow – it was largely destroyed in 1291 as a result of a raid following a dispute over deer poaching, the Black Death struck in 1340 and again in 1350, while in the 15th century Owain Glyndŵr and his rebels dealt it a further blow. There are a number of noteworthy landmarks in the village including Harold Stones (three Bronze Age standing stones) and the Grade 1 listed St Nicholas. Tryleg’s extensive past is subject to ongoing (private) archaeological investigations. And while the spelling of Welsh place names often presents challenges to visitors, Treleck offers some flexibility - historically, up to 30 variations have been recorded, with each of the three roads entering the village using a different version. (E2 - SO501056)

Cleddon Hall – previously known as Ravenscroft, Cleddon Hall is the childhood home of Bertrand Russell - the philosopher, mathematician and notable liberal and pacifist, who won the Nobel Prize for Literature in 1950. (F2 – SO516042)

The Wye Tour –  the Wye Valley is regarded by many as the birthplace of British tourism, with The Wye Tour said to be one of the first ‘package holidays’. Visitors would take a boat tour of the River Wye taking in its dramatic scenery and historic buildings, usually spending two days travelling from Ross-on-Wye to Chepstow. Popularised by the publication of the Reverend William Gilpin’s Observations on the River Wye in 1782, it remained a major destination for British travellers through to around 1850 particularly during the Napoleonic Wars. Gilpin and the Wye Tour are also closely associated with the rise of the Picturesque movement that introduced a new appreciation for the beauty of the natural and built environment. (G2 - SO530002)

Section 15 – Tintern to Chepstow

Tintern – the history of the popular tourist village of Tintern dates back to Roman times when it was a used as a ford for crossing the River Wye. It is believed to take its name from its association with King Tewdrig, a Gwent king who came out of retirement living as a hermit at Tintern to defeat the invading Saxons in battle, before succumbing to his wounds at Mathern. Like the villages further up the valley, Tintern has an industrial heritage and was particularly associated with iron and wire manufacture from the 16th to end of the 19th centuries. The village is most famous for its ruined Cisterican abbey founded in 1131 that has long inspired artists – William Wordsworth has written about it, J.M.W. Turner has painted it, and, it is inspiration behind the Y 100 Sir Fynwy logo. (H2 - SO530002)

St. Mary's Church, Penterry – With sweeping views across the surrounding farms and woodland, St Mary’s church has had an eventful history. Although the surrounding area is now quite remote, Penterry was originally located beside the Roman road (locally called Piccadilly) between the Severn estuary and the small fort at Blestium (now Monmouth). The church is mentioned as early as 955 AD and by the 13th century part of the parish was linked to nearby Tintern Abbey. Penterry is believed to have been severely impacted by the Black Death, with a grove of trees near the church identified as a plague pit. St Mary's fell into disrepair before being restored in the Victorian era, and was again at risk of closure in the early part of the current century until rescued by local residents. (I2 – ST520988)

Piercefield House and Estate – the Grade II* listed Piercefield House is a largely ruined neo-classical country house. It sits within Piercefield Park, a Grade I listed historic landscape that includes Chepstow Racecourse. The Estate was extensively landscaped, in the style of Capability Brown, in the middle of the 18th century when it became a feature of The Wye Tour. The house, designed by noted architect Sir John Soane, was built in the late 18th century. It is rumoured that Admiral Nelson spent a night at Piercefield House, while it is also associated with mixed race sugar planter Nathaniel Wells, who became Britain's first black sheriff when he was appointed Sheriff of Monmouthshire in 1818. Already in decline, the house suffered further damage during WWII when American troops who camped in the park and are reputed to have used it for target practice. (J2 – ST528957)

Chepstow Racecourse – at just under 2 miles Chepstow Racecourse is use for both flat and jump racing including the Welsh Grand National. It also stages indoor and outdoor events, such as concerts with the likes of Tom Jones and Madness. During WWII, the site became RAF Chepstow and featured a grass runway in the centre of the course. It was home to a range of different aircraft including the Hawker Hurricane and Wellington bomber. (K2- ST527951)