![\"Richard](\"https:\/\/www.europesays.com\/britain\/wp-content\/uploads\/2026\/04\/76f5663f49468bd72813a1f8ee6cc629.jpeg\"\/)
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Richard on the border of England and Wales (Richard Collett)<\/p>\n
Croeso i Gymru. The \u201cWelcome to Wales<\/a>\u201d sign flashed past as I crossed over the Severn Estuary, to find the landscape swathed in brooding clouds. Despite the characteristic weather, I was excited to begin my three-day road trip<\/a> along the 160-mile-long border between England and Wales.<\/p>\n Beginning in Chepstow \u2013 where an 11th-century Norman castle guards the southern gateway to Wales \u2013 the border carves a path north towards the Dee Estuary. I was loosely following the route of Offa\u2019s Dyke, an 8th-century earthwork that divided the earliest Anglo-Saxon kingdoms from their Welsh counterparts. It is arguably Britain\u2019s oldest border.<\/p>\n My self-planned itinerary would take me along an ancient divide defended by crumbling medieval castles. I\u2019d follow winding river banks into the Wye Valley<\/a>, traverse the looming Black Mountains and hike historic sections of Offa\u2019s Dyke Path<\/a> on my way north. It\u2019s a route I knew well, having spent the past three years travelling Britain\u2019s borders while researching my new book<\/a>. Although it\u2019s not an \u201cofficial\u201d route, a journey through the Welsh Marches rivals established road trips like Scotland\u2019s NC500, and with far less traffic too.<\/p>\n Richard standing on the English and Welsh border (Richard Collett)<\/p>\n Read more: 10 of the best places to go in Cornwall to avoid the crowds<\/a><\/p>\n From Chepstow, the A466 \u2013 perhaps the most underrated A-road in Britain \u2013 took me along the Welsh bank of the River Wye. Cliffs rose on my left and tall trees cocooned me on the right, before Tintern Abbey\u2019s ragged stone arches appeared in the valley. Tintern Abbey<\/a> has stood in ruins since the Reformation, but it shot to fame in the late 18th century when romantic poets like William Wordsworth inspired the Wye Valley\u2019s first tourism boom.<\/p>\n The \u00a35 parking charge hints at Tintern Abbey\u2019s enduring popularity, and instead, I parked for half the cost at The Old Station<\/a> up the road, from where it\u2019s a two-mile stroll along quiet riverbanks. The Wye Valley\u2019s first tourists enjoyed the same scenic river views from paddle steamers and the Wye Valley Railway, which opened in 1876, brought yet more visitors along a scenic line connecting Chepstow to Monmouth. The paddle steamers and the railway are long gone, but in summer, you can ride a miniature train around Tintern\u2019s Old Station and enjoy afternoon tea on the platforms. For the most part, though, the best way to get around The Welsh Marches these days is by car and on foot.<\/p>\n From Tintern, the A466 weaved back and forth over the River Wye (and back and forth between Wales and England), until Monmouth appeared some 12 miles later. Home to the last fortified medieval bridge in Britain, this Welsh border town was the birthplace of Henry V, the English king who defeated the French at Agincourt. At Monmouth, the border temporarily leaves the River Wye behind, following the River Monnow westwards towards the Black Mountains. I temporarily left the border (and Wales) behind, too, following the A40 along the edge of the Forest of Dean to spend the night in England at the Cross Keys Inn<\/a>, 20 minutes\u2019 drive north.<\/p>\n A rural, 14th-century coaching inn hidden away in the Wye Valley, I was the only overnight guest on this particular Tuesday. A few local foresters kept the bar open until around 8 pm, and after a few pints of Butty Batch beer from the Wye Valley Brewery<\/a>, I was caught in tales of the paranormal.<\/p>\n \u201cThis could be the most haunted pub in the Wye Valley,\u201d I was told, as the bartender soberly explained how the inn\u2019s oldest cellars once doubled up as the village mortuary. \u201cBut don\u2019t worry, your room\u2019s in the newer part. I don\u2019t think it’s haunted.\u201d<\/p>\n At \u00a350 a night, I was happy to brave a ghostly encounter, especially when the Cross Keys Inn<\/a> is just a short drive from spectacular sights like Symonds Yat Rock. I drove westwards from here the next day. I had planned to follow the border over the Black Mountains, where titan-like peaks divide England from Wales.<\/p>\n The route repeatedly crossed the River Wye (Richard Collett)<\/p>\n On a previous trip, I\u2019d crossed Gospel Pass, which, at 549 metres, is the highest paved road in Wales. The weather proved fearsome, however, and I soon discovered the mountain roads were closed indefinitely due to landslides. Instead, I navigated B-roads and country lanes, arriving at Hay-on-Wye<\/a> an hour later.<\/p>\n Famed for its annual literary festival, Hay-on-Wye is perhaps the quirkiest border town in Wales. This was the world\u2019s first \u201cBook Town\u201d and the high street is lined with second-hand book stores. An \u201cHonesty Bookshop\u2019\u2019 occupies the Norman castle\u2019s moat. On the top floor of Hay Castle<\/a>, I uncovered the curious story of Richard Booth. A bookseller and eccentric, on 1st April 1977 Booth declared himself the King of Hay. The castle\u2019s museum preserves Booth\u2019s homemade crown jewels, while Richard Booth\u2019s Bookshop<\/a> is always packed with bibliophiles.<\/p>\n I drove north through an undulating borderland where medieval English kings fought rebellious Welsh princes. In Knighton \u2013 which sits almost exactly halfway along the border, a 45-minute drive from Hay-on-Wye \u2013 I popped into the Offa\u2019s Dyke Centre<\/a> to learn more about the origins of this ancient divide.<\/p>\n Richard Booth’s autobiography, for sale in Hay (Richard Booth)<\/p>\n Read more: The best family-friendly UK holiday destinations for kids and adults of all ages<\/a><\/p>\n Large sections of the border still follow the route laid down by King Offa, an Anglo-Saxon king, more than a thousand years ago. It\u2019s for this reason that the modern border has a justifiable claim to be Britain\u2019s oldest. Outside Offa\u2019s Dyke Centre, you can find some of the best preserved sections of the dyke itself, and if you follow Offa\u2019s Dyke Path down to the river, you can stand on a bridge with one foot in Wales and the other in England.<\/p>\n From Knighton, the A488 took me north into Shropshire, then back into Powys, where I spent the night at the 400-year-old Dragon Hotel<\/a> in Montgomery. Here, yet another crumbling Norman castle holds tales of a bloody medieval borderland that shaped England and Wales. With its grand Tudor facade and home-cooked pie and mash dinners, The Dragon Hotel is the perfect base for exploring the northern reaches of the border.<\/p>\n The next day, I continued north through rolling fields, stopping in Oswestry (a Shropshire town with a sizable Welsh-speaking population), Chirk Castle<\/a> (another Norman castle on the border) and the dramatic Pontcysyllte Aqueduct<\/a> before turning back at Wrexham. The border itself continues onto the Dee Estuary, and if you\u2019re not castled out yet, you can finish the drive at Flint Castle, a 1.5-hour drive from The Dragon Hotel.<\/p>\n Packed with history, country pubs and ever-changing scenery, a road trip along the Anglo-Welsh border is a serious contender to Scotland\u2019s NC500. The difference? Here in the Welsh Marches, you’re only likely to get stuck behind a tractor, rather than a queue of campervans.<\/p>\n Richard Collett is the author of Along the Borders: In Search of What Divides and Unites the British Isles<\/a>. Published on 30th April by Doubleday.<\/p>\n How to do it<\/p>\n This isn\u2019t an established or marked road trip route, so you\u2019ll need to plan your journey along the Anglo-Welsh border using Google Maps or similar. Doubles at the supposedly haunted Cross Keys Inn<\/a> start from \u00a350 per night, room only.<\/p>\n![\"Richard](\"https:\/\/www.europesays.com\/britain\/wp-content\/uploads\/2026\/04\/afbb67b2fe7a4a89540970d1eb4a8bfd.jpeg\"\/)
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<\/p>\n![\"Richard](\"https:\/\/www.europesays.com\/britain\/wp-content\/uploads\/2026\/04\/17387aae8c2c2fed4910a7191731127c.jpeg\"\/)
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