Self-guided Offa's Dyke Path: South

Check into your family-run guest house in the heart of Chepstow. This afternoon, why not visit Chepstow castle, the oldest surviving castle in Wales dating from 1067. Or perhaps take a stroll through this mediaeval town. Chepstow, which means marketplace in Old English, is a great place for a little shopping. You’ll find plenty of tempting independent boutiques amid the handsome Georgian and Victorian buildings in the centre of town.

Following a welcome meeting with your tour leader, get to know your fellow travellers over dinner this evening, ahead of your epic journey together along the Welsh-English border.

Enjoy a hearty breakfast ahead of the first day of your journey. After a short taxi transfer to the start point at Sedbury Cliffs, your first day’s hiking will cover around 12 kilometres through a semi-ancient wooded valley and along picturesque rivers with some incredible viewpoints, including the Devil’s Pulpit. The Devil’s Pulpit is a viewpoint and limestone rock jutting out from the cliffs high above the River Wye offering breathtaking views over Tintern Abbey.

To complete your first walk, drop down into the picturesque village of Tintern, which hugs the River Wye at this point. Take time to visit Tintern Abbey, a national icon standing on the banks of the River Wye since it was founded in 1131 by monks of the Cistercian Order, or enjoy a self-guided vineyard tour at Parva Farm Vineyard. Check into your beautiful accommodation for the night, where your luggage will be waiting for you

After breakfast, follow the River Wye as you leave Tintern behind and set off on the next stretch of Offa's Dyke Path.

Enjoy the relatively flat first half of today’s walk as you follow the River Wye’s edge, before climbing steadily up through the beautiful semi-ancient woodland of the Wye Valley Area of Outstanding Natural Beauty. As you near the outskirts of Monmouth town, pause to explore The Kymin, a charming 18th-century Round House and Naval Temple. Make sure you pay a visit to Monmouth Castle and Monnow Bridge, Great Britain’s only remaining fortified river bridge, in the centre of town before you head to your boutique hotel for the night.

Monmouth has officially been named as the UK’s first Bee Town, thanks to the local council’s work to make the town a better place for pollinators. Why not visit the Bees for Development shop in town, selling handmade gifts to support beekeepers in the poorest communities.

Today’s stretch of Offa’s Dyke Path is around 23 kilometres, leaving Monmouth behind and heading to the small village of Llangattock Lingoed. As you walk through the open countryside, you may be able to spot The Kymin behind you.

Take in the incredible landscape as you climb through King’s Wood, across open farmland and along the River Trothy. Offa’s Dyke Path leads you past the mediaeval Llanvihangel-Ystern-Llewern church, a 15th century active parish. Back in the open landscape, you might see the mountains of Skirrid and Sugar Loaf visible in the distance.

Take a moment on your way to explore the serene White Castle, the best preserved and most imposing of the trio of Monmouthshire fortresses known as the ‘Three Castles’. Continue on your way to reach the small village of Llangattock Lingoed - as you pass the pretty white pre-Norman church of St Cadoc on the edge of the village, take a moment to head inside and view the impressive early 15th century wall painting. Relax this evening and enjoy a well-deserved drink in the local pub.

After another hearty breakfast (it’s a good job you’re doing so much walking!), continue on your way along Offa’s Dyke Path, through rolling fields and farmland as you leave Llangattock Lingoed behind.

Today’s route crosses the highest point along the southern section of Offa’s Dyke Path at Hatterall Ridge as you walk through the stunning Black Mountains.

Traverse your way down from the Black Mountains plateau to arrive at your home for tonight, a homely pub in the village of Longtown.

After breakfast has settled it’s time to hike back up to the top of the Black Mountains plateau within the Bannau Brycheiniog national park where you can continue soaking up the stunning vistas. Keep an eye out here for herds of wild ponies, birds of prey and views to the Vale of Ewyas. This is also a popular paragliding spot so keep your eyes peeled for brightly-coloured parachutes filling the sky above!

Just before reaching Hay Bluff, you’ll make your final descent into Hay-on-Wye, world-renowned for its books and bookshops.

Spend your last evening celebrating your awesome achievement relaxing at your traditional inn, or head into the bustling market town for a few well-earned Welsh beers.

After breakfast it’s time to depart having completed the first section of this epic long distance walking route!

If you require assistance with onward travel or accommodation to extend your time in Wales, or if you’d like to head straight into the next stage of the Offa’s Dyke Path, please let us know when you enquire about dates. We’ll be happy to help with any additional arrangements you need.