Offa’s Dyke Path South: Chepstow to Knighton

Chepstow to Redbrook

The opening 1.5 miles from Sedbury Cliffs to the edge of Chepstow offer a gentle introduction to what is a truly superb long-distance walk, and are best seen as a brief prelude to the landscapes that lie ahead.

Beginning at the southern end of the route means you are immediately walking alongside Offa’s Dyke itself, unlike at the northern end where signs of the Dyke do not appear until much later at Castle Mill.

In these first few miles, the trail gives you an early taste of the ancient earthwork, leading through fields and past Buttington Tump before briefly passing through the outskirts of Chepstow. It’s worth keeping a close eye on your guidebook and it’s detailed maps, as well as the acorn waymarkers on lamp posts and gates, as this initial section can be easy to miss if you are not paying attention.

Once beyond Chepstow and its surroundings, the route soon begins to reveal more of its character. The section onwards to Monmouth makes for a rewarding day’s walk, though many walkers choose to ease into the trail by dividing it into two stages. Tintern is an excellent option for an overnight stop. While it may feel like an early pause, it can be a wise choice, allowing your legs to settle into the rhythm of the walk and leaving you well prepared for the longer and more demanding days still to come.

Those walking into Tintern are rewarded with the magnificent riverside ruins of Tintern Abbey, one of the standout highlights of the early stages of the walk. For those continuing directly on to Redbrook, the Abbey still makes a memorable appearance, offering an enticing glimpse through the trees from the path high above the River Wye.

Redbrook to White Castle

This section leads through gently undulating countryside, with the land gradually rising towards the Black Mountains. Leaving Monmouth and the River Wye behind, the path begins to reveal a quieter, more rural character as it meanders northwards.

The route follows Watery Lane, passing the edge of a housing estate before opening out into pleasant fields that lead on to King’s Wood, a mixed woodland of broadleaved trees and conifers. Depending on the day, you may hear the sounds of forestry work nearby, adding to the sense of this being a working landscape as well as a beautiful one.

Emerging from the trees, the path passes The Hendre before continuing across more fields to Abbey Bridge. This is the most visible reminder of the former Cistercian abbey of Grace Dieu, founded in 1226 by John of Monmouth and later destroyed during the reign of Henry VIII. Although no visible remains survive, it is easy to imagine the importance this site once held. Just before reaching the bridge, keep an eye out for the rare White Park cattle, a distinctive and memorable sight along the way.

A few fields beyond the bridge, the route rejoins the River Trothy, which accompanies you as far as Llanvihangel-Ystern-Llewern. The small church of St Michael is one of the many charming churches found along Offa’s Dyke Path, adding another layer of history to the walk.

From here, cider apple orchards and the B4233 guide you onwards to Llantilio Crossenny and ultimately to White Castle.

White Castle to Hay-on-Wye

Leaving White Castle behind, the route continues through peaceful border countryside towards the charming village of Llangattock Lingoed, where a small cluster of houses, a welcoming pub and the whitewashed church of St Cadoc make for a delightful point along the way.

From here, the trail continues towards Pandy before beginning its ascent onto the long spine of the Hatterall Ridge and the highest point of Offa’s Dyke Path at 2,360 feet (713m). This is one of the most memorable sections of the entire route, combining a wonderful sense of journey with some of the finest scenery on the trail.

Rather than tackling the ridge in a single push, we break this section with an overnight stay in Longtown. This is a lovely way to experience the landscape, allowing time to enjoy the dramatic setting of the Black Mountains and to fully appreciate the ridge walk without feeling rushed. Splitting the stage here turns it into one of the true highlights of the trail, giving you the chance to savour both the ascent and the wide-open views.

The route initially leaves the A465 through fields and quiet lanes before climbing steadily towards Hatterall Hill. Once on the ridge, the walking is generally good underfoot, with sections supported by substantial flagstones laid as part of an erosion-control programme by the Brecon Beacons National Park Authority.

With clear weather, this stretch offers some of the grandest walking on Offa’s Dyke Path, with sweeping views across the border country and a wonderful sense of space and elevation. The descent from Hay Bluff is particularly memorable, leading you gradually down towards the valley and onwards across moorland and farmland to the book town of Hay-on-Wye.

Hay-on-Wye to Kington

This stage includes another strong contender for the finest section of the entire trail: the crossing of Hergest Ridge, an open common grazed by sheep and wild ponies. From the ridge, there are wonderful views across the Shropshire Hills, while behind you the outline of Hay Bluff and the Black Mountains gradually fades into the distance.

Underfoot, the walking here is a pleasure, with soft springy turf that has been grazed by sheep for centuries. The ridge has long been shaped by the farming traditions of the area, and in late summer you may see cut bracken baled in the fields, used locally as bedding for livestock.

Before reaching the ridge and on to Kington, the route first draws you onwards through ten memorable miles to the small village of Gladestry. Leaving Hay-on-Wye and the River Wye behind once more, the path passes through Bettws Dingle, a shaded wooded glen that offers a lovely contrast to the open country still to come.

A short section of road walking leads to Newchurch before the trail rises over Disgwylfa Hill, where fantastic panoramic views begin to open out. From here, more open countryside leads you to Gladestry, the southern gateway to Hergest Ridge and the onward route to Kington.

This is a section to enjoy at a leisurely pace, taking time to appreciate the ever-changing views and the sense of space that makes this stretch so memorable.

Kington to Knighton

This section fits comfortably into a day’s walking and offers some truly marvellous stretches of the trail. Between Kington and Knighton, the route passes through wonderfully open country with minimal habitation, giving you long periods where it feels as though you have the landscape – and the Dyke itself – entirely to yourself. Several impressive sections of Offa’s Dyke are visible along the way, in places standing high and distinct with its accompanying ditch clearly defined.

Leaving Kington, the open hilltops soon begin to beckon, though first the route passes close to Kington Golf Club, the highest 18-hole golf course in England. The clubhouse is known for being welcoming to walkers and can make a handy stop for refreshments or any last-minute waterproof essentials.

Beyond Rushock Hill, the scenery becomes wonderfully varied, with bracken and gorse, open heathland and pockets of woodland combining to create a constantly changing landscape. It is a section full of atmosphere, often accompanied only by the wind, and the sight of soaring buzzards, with the occasional red kite adding to the sense of wildness.

Further switchbacks and gently rolling farmland follow, with several enjoyable stretches walking directly alongside the Dyke. Dolley Green may be little more than a point on the map, but it lies close to the attractive town of Presteigne, which is well worth a short detour if time allows.

The route then crosses Furrow Hill and Hawthorn Hill, both offering fine, airy walking and uplifting views, before continuing through farmland and onwards towards the final descent into Knighton, where another memorable day on the trail comes to a close.