Three Castles Walk Walking Holidays
An 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.

- Nights
- 2 to 4 Nights
- Distance
- 20 to 20 miles
- Location
- South Wales
- Difficulty
- Easy to Moderate – Moderate
- Season
- Mar to Oct
- Price from
- £275
Highlights
Castle to Castle: The Three Castles Walk
- Grosmont Castle
- Impressive Norman ruins with panoramic views across the Monnow Valley
- Skenfrith Castle
- A war-scarred fortress linked to the revolt of Owain Glyndŵr
- White Castle
- An impressive Norman fortress with moat and drawbridge
- Market towns
- Finish in the charming towns of Monmouth and Abergavenny
- Countryside
- Walk through rural valley scenery beneath the Black Mountains
- Historic stay
- Stay in a converted 17th century former 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.

Choose Your Walk
Our 3 Castles Walk Itineraries
Caggle Street to White Castle
19 miles (30.6 km)From £575 Per Person
From £450 Per Person
Caggle Street to Llangattock Lingoed
22 miles (35.4 km)From £395 Per Person
From £275 Per Person
Key Information
- 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
Customise your trip?
Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs.
- Telephone
- +44 (0)1291 689 774
3 Castles Walk Client Reviews
4.8/5 based on 18 reviews
"THis was a very good experience with all our questions answered promptly, prior to the hike, good material provided."
"Very good, clear communication at all times"
"Good set up with transfer and pick up. Great b&b accommodation and proximity to pub. Super helpful and knowledgeable host."
"Friendly, professional, well researched"
"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."
"Good accommodation, and excellent information packs for the walk."
"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."
"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."
"Our accommodation was fantastic! Couldn't have done more. 5/5"
Hand-Picked Accommodation: Comfort Along the Way
We seek out the best accommodation of its type available

Points of Interest
Three Castles
The castles were built in relation to each other, their trilateral positioning being key to holding down the strategic military point of Monnow Valley. They were originally built following the 11th century Norman conquests, with sections added in the 12th and 16th centuries.
The castles are free to visit, and visitors can walk up to the ramparts - here you have an exceptional vantage point over the rural Welsh countryside to the Skirrid Mountain in the distance. Read more on the history of the castles here.

Media Gallery
Customise your trip?
Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs.
- Telephone
- +44 (0)1291 689 774
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