Walk 
2 to 4 nights
19 to 22 mls (km)
South Wales
Easy to Moderate 
Mar to Oct
£245
Castle to Castle: The Three Castles Walk
- Your walks link the trilateral castles built as part of the Norman conquest of Wales:
- Grosmont Castle - one of the more complete, at the centre 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
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 monk's path, along quiet riverbanks and an energetic ascent over Graig Syfyrddin descending to the sleepy little village of Grosmont with 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 around Skenfrith Castle and its gem of 13th century 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 (Ysgyryd Fawr) and the Brecon Beacons (Bannau Brycheiniog).
Path Walkthrough
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 (a.k.a. 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.
Our Three Castles Walk Itineraries
Caggle Street to White Castle
Distance: 19 miles (30.5km)
- 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
You choose which day you would like your holiday to start on. We will book your holiday in accordance with your requirements.
Our Three Castles Walk holidays are available to walk March to October.
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 - ideal for getting outdoors and spending the day walking through the countryside in the sunshine.
📷View of Sugar Loaf from White Castle
📷Skenfrith Castle
📷County Scene Abergavenny
📷Village of Grosmont
📷White Castle
📷Grosmont Castle
📷Skenfrith Castle
📷Autumn countryside scene ry, Abergavenny
Three Castles Walk Client Reviews
4.9/5 based on 14 reviews
My friend and I had the most wonderful time on our walking holiday. Happy memories to treasure. Thank you so much Celtic Trails, for a wonderful caring experience and excellent organisation.
Cathy H - May 2024
Good accommodation, and excellent information packs for the walk.
Joana NZ - July 2023
I found your company very professional and reliable whilst also approachable and friendly. The arrangements were perfect and the accompanying guides and supporting information accurate and invaluable. We particularly valued the local knowledge. An uplifting experience in beautiful countryside, any effort and stress associated with organising this type of holiday was obviously absorbed by yourselves leaving us free to enjoy ourselves.
Anon - June 2023
Celtic Trails were easy to work with. The 3 Castles Walk was a great entree to a beautiful place. We felt cosseted. A lovely accommodation and host.
Anon - July 2022
Our accommodation was fantastic! Couldn't have done more. 5/5
Anon - September 2021
Great to have an aim to the walk - visiting the 3 castles en-route. Great walk with all the organisation covered - relaxingly sorted out by Celtic Trails - thank you. LOVED the marked up OS map and detailed instructions. All good.
Anon. - May 2019
We loved the views and the variety of countryside.
Giles - June 2018
Very muddy path but a great adventure.
Grindstaff - April 2018
"The host of our accommodation could not do enough for us. Would recommend."
Whysall - March 2018
"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!"
Noonan - April 2017
"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."
Spence - September 2016
"We would love to do one of your walks again! 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!"
Bushby - September 2016
‘"Great hosts and very amenable. Pub food in the village good and staff very friendly and helpful. Overall a great short break. Thank you."
Greer - August 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."
Warren - September 2015
