Hiking the Three Castles Walk

by Karen Simons

The Three Castles Walk, visiting Grosmont, Skenfrith and White Castle, enjoys twenty miles of the most spectacular views that the Welsh Borderlands can offer. It's a circular trail, and we arrange it as a single centre tour, so you can settle down in one accommodation for the duration.

Three Castles Monmouthshire

Enjoying the Three Castles Walk

I stayed close to Grosmont in dog-friendly accommodation so that I could walk with my two dogs. The idea was to rewrite the route notes as well as enjoy a few days away from the office.

While the route might be circular, it’s shaped more like a triangle, with a castle at each point. We divide the trail into three sections, from castle to castle, for our standard itinerary.

Three Castles Walk map

Grosmont to Skenfrith

From Grosmont, the trail climbs up to give good views back to the village church and castle, before wandering south over rolling farmland to join the River Monnow as it flows towards Skenfrith, the next castle. Skenfrith church and castle were both a delight. The church houses an ancient relic of a medieval cope (cape) and the tomb of the last governor of the Three Castles.

Walking Grosmont to Skenfrith on the Three Castles Walk Views over Monmouthshire Skenfrith Church on the Three Castles Way

Skenfrith to White Castle

Leaving Skenfrith, we walked west through changing scenery towards Offa’s Dyke Path and White Castle. The paths were quiet, with only sheep for company.

A line of sheep on the Three Castles Walk

White Castle is my favourite of the castles on this holiday. It has a wonderful stone-lined moat and outer curtain walls. The fortifications date from 1066, when protection was needed for the Welsh Marshes and the Three Castles were formed under one lordship to defend the area from a Welsh invasion.

Crossing a stile on the Three Castles Walk Entering White Castle Views from White Castle

White Castle to Grosmont

The final stretch of the trail, heading north now on its return to Grosmont, has spectacular views in all directions with a final climb up to walk along a wooded path before descending to the historic church and castle. Again, both are well worth a visit and a climb up the ruins of Grosmont castle gives a great final photo shot of this pretty little village.

Looking out across Monmouthshire Walking to Grosmont on the Three Castles Walk Grosmont Castle

Trail complete, we walked back to our accommodation for a celebratory cream tea on the lawn. 

Celebratory cream teas in Grosmont

Contours Holidays pride ourselves on our expert knowledge of the UK's trails. We regularly set out to check our routes and directions and to make improvements on the holidays we offer. You can find several write-ups of staff expeditions in our Trail Diaries.

Originally published 16/08/19

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Try the Three Castles Walk

  • Explore the wonderful history of the three border castles of Grosmont, Skenfrith and White Castle.

  • Complete the challenging walk over Graig Syfyrddin, with views of The Sugarloaf and the Black Mountains.

  • Absorb the tranquil surroundings of Monmouthshire and the Monnow Valley.

© Contours Walking Holidays Three Castles Walk map
Circular trail beginning at Llangattock-Lingoed
20 miles (32 km)
2nd January to 24th December

Try the Three Castles Walk

Code Tour Duration Difficulty Price per person
3CW1 A circular trail beginning at Grosmont(T) 3 nights, 2 days walking Moderate £370
3CW2 A circular trail beginning at Grosmont(T) 4 nights, 3 days walking Easy £490