Castle to Castle: The Three Castles Walk

A historical route through Welsh countryside, linking three castles on a short walking break in the Monnow Valley.
Find peace of mind following quiet rural trails through this little known corner of Monmouthshire, an unspoilt, picturesque landscape that has remained largely unaffected by the ages.

Highlights
  • Your walks links the trilateral castles built as part of the Norman conquest of Wales:
    • Grosmont Castle - One of the more complete, at the center of a pretty village
    • Skenfrith Castle - One of the most war-scarred castles, featured in the revolt of Owain Glyndŵr
    • White Castle - Cuts an impressive figure with a surrounding moat and drawbridge over the river Monnow
  • Finish your short break with a visit to the charming market towns of Monmouth and Abergavenny
  • Walk through rural, valley scenery, set against the surrounding Black Mountains
  • One of our shorter walking holidays, staying in a converted former 17th century rectory
  • 2 to 4 nights
  • 22 mls (view km)
  • Nr Abergavenny, South Wales
  • Moderate
  • Mar to Oct
  • £220

A Short Walking Holiday Break

The Three Castles Walk links the Trilateral Castles, a triangle of Norman castles built by Hugh de Burgh, to maintain a grip and a line of defence along the turbulent Welsh Marches. Walking through the quiet Welsh border countryside of sheep pastures and patchwork fields, it is hard to imagine the peaceful countryside as the backdrop of fierce medieval conflicts.

You will walk old monks path, along quiet riverbanks and an energetic ascent over Graig Syfyrddin descending to the sleepy little village of Grosmont to its castle, fine church, old market hall and narrow main street, scene of dramatic encounters between Henry III and Llewellyn’s fierce Welshmen in 1233.

From Grosmont, you follow the trail through the Monnow valley to the tiny hamlet of Skenfrith on the meandering river Monnow. Time appears to have stood still, as you find yourself amongst the picturesque rows of cottages that have sprung up around Skenfrith Castle and its gem of a C13 church and wooden belfry.

Your walk then takes you to White Castle (Castell Gwyn), which remains well preserved within the fortifications and moat encompassing. The castle looms over the peaceful, surrounding farmland, with views across to the Black Mountains, the Skirrid (called Holy Mountain) and the Brecon Beacons.

Path Walkthrough

Three Castles Walk map
Our Three Castles walking route links the famous castles of the Monmouthshire area

Walkers can expect a landscape very typical of rural Wales, with farmland, fields and wooded hills, and the going underfoot fairly wild outside of the country lanes and winding market town streets. The path is generally easy, but there are some undulating sections, as well as untamed parts of the path - which can make progress harder. The areas quiet nature, with farm and storehouses being the most developed use of the land, may account for some of the more unruly and less beaten parts of the path.

The part of South Wales is renowned for its scenic walks, and traveling from White Castle to Grosmont over Graig Syfyrddin (aka Edmund's Tump), you'll find picturesque views over the Marches and the Black Mountains of South Wales. From Grosmont, you'll be able to stop at the pretty village surrounding the castle before heading over to Skenfrith, on the banks of the river Monnow.

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Three Castles Walk Walking holiday

Our Three Castles Walking Holiday Itineraries

Prices are per person, based on two people sharing, single person supplements apply.

Caggle Street to Llangattock Lingoes via White Castle

Length: 19 miles/30.4km | Difficulty: Easy to Moderate

CodeDurationStart Price 
3CW13 nights, 2 days£275 (pp)View Itinerary
3CW22 nights, 2 days£220 (pp)View Itinerary

Caggle Street to White Castle

Length: 22 miles/35.2km | Difficulty: Easy to Moderate

CodeDurationStart Price 
3CW34 nights, 3 days£355 (pp)View Itinerary
3CW43 nights, 3 days£300 (pp)View Itinerary

Optional continuation of walk for an extra 3 miles/4.8km directly on to accommodation on last walking day of 3CW3 & 3CW4 itineraries.

Caggle Street to Llangattock Lingoes via White Castle

Three nights, Two walking days
Price: £275 (pp)
Holiday Code: 3CW1
DayLocationsDistance
Day 4:Departure Day
Day 1:Arrival Day
Day 2:Caggle Street to Skenfrith Castle via Grosmont11.5 miles/18.4km
Day 3:Skenfrith to Llangattock Lingoed via White Castle10.5 miles/16.8 km

Itinerary Information: Three nights accommodation with two walking days. Arrive in Abergavenny on day one, start walking from day two and depart from accommodation on morning of ay four.

Departure Dates: This itinerary can be walked any time between Mar to Oct. You simply choose which day you would like your holiday to start on.

Rest Days: Should you wish, rest days can be taken at stops along the route, view details.

What's Included: view full details.

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Caggle Street to Llangattock Lingoes via White Castle

Two nights, Two days
Price: £220 (pp)
Holiday Code: 3CW2
DayLocationsDistance
Day 3:Skenfrith to Llangattock Lingoed via White Castle - Departure at end of the day10.5 miles/16.8 km
Day 1:Arrival Day
Day 2:Caggle Street to Skenfrith Castle via Grosmont11.5 miles/18.4km

Itinerary Information: Two nights accommodation with two walking days. Arrive in Abergavenny on day one, start walking from day two and depart from Llangattock Lingoed following end of walk.

Departure Dates: This itinerary can be walked any time between Mar to Oct. You simply choose which day you would like your holiday to start on.

Rest Days: Should you wish, rest days can be taken at stops along the route, view details.

What's Included: view full details.

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Caggle Street to White Castle

Four nights, Three days
Price: £355 (pp)
Holiday Code: 3CW3
DayLocationsDistance
Day 5:Departure Day
Day 1:Arrival Day
Day 2:Caggle Street to Grosmont Castle6 miles/9.6km
Day 3:Grosmont to Skenfrith Castle5.5 miles/8.8 km
Day 4:Skenfrith to White Castle7.5 miles/12 km

Itinerary Information: Four nights accommodation, with three walking days. Arrive in Abergavenny on day one, start walking from morning of day two and depart from accommodation on morning of day five.

Departure Dates: This itinerary can be walked any time between Mar to Oct. You simply choose which day you would like your holiday to start on.

Rest Days: Should you wish, rest days can be taken at stops along the route, view details.

What's Included: view full details.

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Caggle Street to White Castle

Three nights, Three days
Price: £300 (pp)
Holiday Code: 3CW4
DayLocationsDistance
Day 4:Skenfrith to White Castle - Departure at the end of the day7.5 miles/12 km
Day 1:Arrival Day
Day 2:Caggle Street to Grosmont Castle6 miles/9.6km
Day 3:Grosmont to Skenfrith Castle5.5 miles/8.8 km

Itinerary Information: Three nights accommodation with three walking days. Arrive in Abergavenny on morning of day one, start walking from day two and depart from accommodation on morning of day four.

Departure Dates: This itinerary can be walked any time between Mar to Oct. You simply choose which day you would like your holiday to start on.

Rest Days: Should you wish, rest days can be taken at stops along the route, view details.

What's Included: view full details.

Back to all itineraries

  • What's Included?

    We include:

    • Good standard accommodation in a country house or 13th century character Inn, with en-suite or private facilities, full cooked breakfast, packed lunches
    • Personal transfer between accommodation and path where necessary
    • We also provide a Walk Pack including trail booklet, information book about the 3 castles, itinerary and walking break planning
  • Price Info.

    Bank Holidays & Short notice bookings may incur extra charges.

    Single supplements 

    Solo person bookings: £25 per night

    Where singles are walking as part of a larger group and are willing to share a Walk Pack: single room occupancy supplements will apply.

    Postage Overseas: £5.00 (Europe) £10.00 (Rest of the World) per walk pack

  • Getting There

    The nearest train station, Abergavenny, is served by hourly trains running from London Paddington (an average journey time of 2½ hours).

    Celtic Trails can arrange to collect and return you to Abergavenny Station to the start of the route for a charge of £20 each way.

  • Best Time to Travel

    Weather conditions in Wales are not too dissimilar from the rest of UK, albeit when travelling through Wales we advise carrying a waterproof jacket as you can never rule out the possibility of showers.

    Please note that some sections can be particularly muddy after prolonged wet spells across the area.

    That being said, in the summer months these wet spells are a lot less prolonged than the winter months, ideal for getting outdoors and spending the day walking through the countryside in the sunshine.

    Rainfall when walking in Wales                                                                Walking weather Wales                                                    Walking weather South Wales

Client Reviews of Our Three Castles Walking Holiday

Our past clients rated this walk 4.9 out of 5, read a selection of 5 reviews below.

"We found Celtic Trails to be better than other companies, and Karen & Paul are perfect hosts, informative, helpful, gracious and witty. We spent four days there, loved every one. Plus, The Three Castles hiking was wonderful!"

4.9 out of 5

April 2017

‘"Great hosts and very amenable. Pub food in the village good and staff very friendly and helpful. Overall a great short break. Thank you."

5 out of 5

August 2016

"This walk surpassed my expectations in terms of scenery – it was stunning. Celtic Trails organisation made it carefree. Distances were perfect for a relaxed holiday."

5 out of 5

September 2016

"We would love to do one of your walks again! The luggage and transportation, support and great accommodation. We enjoyed that the trail led through beautiful country, the views, the sheep + cow, the castles – and at the end of the day, a very comfortable and welcoming place to stay!"

4.8 out of 5

September 2016

"This is our 6th walking holiday, so we have a good understanding of these tours. We could not fault Celtic Trails for quality & communication, administration, accommodation & assistance. Thank - you all."

4.8 out of 5

September 2015

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