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
From £275 per person
Book

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).

Walls and remains of a 12th Century, Grosmont Castle

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.

Three Castles Walk map

Choose Your Walk

Our 3 Castles Walk Itineraries

Caggle Street to White Castle

19 miles (30.6 km)

Caggle Street to Llangattock Lingoed

22 miles (35.4 km)

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.

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."

D Reid, Nova Scotia
September 2025

"Very good, clear communication at all times"

Mr & Mrs J R Shiels
July 2025

"Good set up with transfer and pick up. Great b&b accommodation and proximity to pub. Super helpful and knowledgeable host."

Karen and Mark from Surrey
April 2025

"Friendly, professional, well researched"

Richard
March 2025

"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

Hand-Picked Accommodation: Comfort Along the Way

We seek out the best accommodation of its type available

Hand-Picked Accommodation: Comfort Along the Way

Points of Interest

Three Castles Walking Holidays South Wales

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.

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