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South East Wales, and Monmouthshire in particular, holds one of the richest concentrations of castles anywhere in Britain, a legacy of centuries spent as contested Marcher territory along the border with England. Cycling through this landscape of gentle river valleys, rolling farmland and dramatic mountain fringes, it is entirely possible to go a full day without being out of sight of at least one ruined stronghold, each with its own story to tell about the turbulent history of this beautiful corner of Wales.
The journey begins around Chepstow, home to the oldest surviving post-Roman stone castle in Britain, perched dramatically above the tidal cliffs of the River Wye. From here, the lower Wye Valley offers some of the finest riverside cycling in Wales, much of it along the traffic-free Wye Valley Greenway, passing beneath wooded limestone cliffs and close to the atmospheric ruins of Tintern Abbey on the way towards the historic border town of Monmouth, with its remarkable fortified medieval bridge still standing guard over the River Monnow.
North of Monmouth lies the heart of castle country, the celebrated Three Castles of Gwent at Skenfrith, Grosmont and White Castle. Built by the Normans as a coordinated trio to control this strategically vital stretch of border country, all three remain wonderfully atmospheric ruins today, set within the quiet, unspoilt countryside of the Monnow Valley. Cycling between them along quiet lanes, past small vineyards and cider orchards, offers a real sense of stepping back into the medieval Marches.
From the Three Castles, the landscape changes dramatically as the route climbs towards the Black Mountains and the Vale of Ewyas, a steep-sided, remote valley leading up towards Gospel Pass. Here lie the beautifully atmospheric ruins of Llanthony Priory, a twelfth-century Augustinian priory set against a backdrop of genuinely dramatic mountain scenery, one of the most memorable sights on the whole route and a world away from the gentler valleys further south.
The journey continues through Abergavenny, gateway to the Black Mountains and Bannau Brycheiniog National Park, and on through the rolling countryside around Usk, passing the grand ruins of Raglan Castle, one of the finest surviving examples of late-medieval castle architecture in Britain, before returning towards the Wye Valley to complete the loop. It is this combination, quiet valley cycling, an exceptional density of historic castles, and a real taste of the Black Mountains along the way, that makes Valleys and Castles such a rewarding and varied introduction to South East Wales.
This self-guided cycling tour of South East Wales is a perfect active holiday choice for families, or for anyone wanting a relaxed but genuinely interesting week in the saddle without the logistics of long-haul travel. There are no fixed departure dates, giving you the flexibility to travel whenever suits you best. The package includes pick-up and drop-off at either Abergavenny or Hereford railway station, quality accommodation each night in comfortable B&Bs and guesthouses, daily luggage transfer, custom maps with your route highlighted, a detailed route guide, and a well-equipped 27-speed hybrid bike complete with handlebar bag, puncture repair kit, cycle computer, first aid kit, lock and water bottle. Emergency vehicle back-up is available throughout your trip.
Day 1: Arrive in Chepstow Make your own way to Chepstow, and take some time to explore its castle, the oldest surviving stone castle in Britain, before settling in for the evening.
Day 2: Chepstow to Monmouth Follow the Wye Valley Greenway and quiet lanes up the beautiful lower Wye Valley, passing close to Tintern Abbey, on the way into the historic town of Monmouth.
Day 3: Monmouth to Skenfrith A gentle ride up the Monnow Valley, past small vineyards and orchards, to the pretty village of Skenfrith and the first of the Three Castles of Gwent.
Day 4: Skenfrith to Llanthony Priory Continue via Grosmont and its own castle ruins before climbing into the dramatic Vale of Ewyas to reach the beautifully atmospheric ruins of Llanthony Priory, set against the Black Mountains.
Day 5: Llanthony to Abergavenny A memorable day descending from the mountains into Abergavenny, gateway to the Black Mountains and Bannau Brycheiniog National Park, with plenty to explore in the town itself.
Day 6: Abergavenny to Usk Quiet lanes lead through rolling Monmouthshire countryside to the handsome market town of Usk, with a detour to the impressive ruins of Raglan Castle along the way.
Day 7: Usk to Chepstow The final day completes the loop back towards the Wye Valley and Chepstow, with the option to visit White Castle, the best preserved of the Three Castles, along the way.
Day 8: Depart Enjoy a final morning in Chepstow before making your way home.
(Itinerary shown as an example – this tour typically runs 6-8 nights and can be adjusted to suit fitness levels, interests and available time.)
