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Three Castles Walk

A single-centre, circular walking holiday around Monmouthshire, beginning and ending in Grosmont.

3 to 4 nights
20 miles
Easy to Moderate

From £265 per person

Discover the available tours

About this route

In the centuries following the conquest of 1066, the Normans built a triangle of castles in Monmouthshire to control the turbulent border between England and Wales. The Three Castles Walk tours between them, through verdant pastures and peaceful woodland.

It begins with ruined Grosmont Castle, with its crumbling walls and rounded gatehouse, before wandering to Skenfrith Castle, which stands in a loop of the river in the centre of its village.

The trail saves the enormous, well-preserved fortress of White Castle for last, with its powerful round towers and beautiful views over the scenery the Three Castles Walk has explored in the days before.

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

Holiday highlights

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

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

Absorbing the tranquil surroundings of Monmouthshire and the Monnow Valley.

Available tours

CodeTourDurationDifficultyPrice per person
3CW1 A circular trail beginning at Grosmont(T) 3 nights, 2 days walking Moderate£265
3CW2 A circular trail beginning at Grosmont(T) 4 nights, 3 days walking Easy£350

Three Castles Walk 3 nights, 2 days walking

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Travel info
  • Weather

Important information

The Three Castles Walk is a single centre holiday based in the village of Grosmont. Where your walking day does not end in Grosmont, we will provide transfers to collect you from the trail at the end of your walking day and return you to the trail in the morning.


Travel to Grosmont (Wales)(T) where your accommodation has been booked

Day 1

Grosmont(T) to White Castle. 12.5 miles (20km)
Transport is provided to collect you from White Castle and return you to Grosmont (Wales)(T).

Day 2

White Castle to Grosmont(T). 7.5 miles (12km)
Transport is provided to take you from Grosmont (Wales)(T) to White Castle on the morning of your walk.


Depart from Grosmont (Wales)(T) after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation; should your accommodation be further than this, transfers will be provided as standard.

Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£45.00 per person / per night
Single Supplement
£35.00 per person / per night

You can add rest days at the overnight stop:

Extra night (Standard)
£55.00 per person / per night

What's included?

  • 3 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

The Three Castles Walk is a single centre holiday, meaning that you are based in Grosmont throughout the tour. However, if you would like to spend more time exploring Grosmont, its castle and the surrounding area, an extra night could be the perfect way to extend your holiday.

If you wish to spend more time walking in the area, Grosmont lies in the valley of the River Monnow and there are a range of shorter walks and trails that leave the village.

You can add rest days at the overnight stop:

Extra night (Standard)
£55.00 per person / per night

Tour Facts

Total distance: 20 miles (32 km)
Duration: 3 nights, 2 days walking
Minimum daily distance: 7.5 miles (12 km)
Maximum daily distance: 12.5 miles (20 km)
Code: 3CW1 Grade: Moderate
Season: 2nd January - 24th December
Start of holiday: Grosmont(T)
End of holiday: Grosmont(T)

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air - The most convenient major city and international airports are Cardiff and Bristol.

By Rail - The nearest rail stations to Grosmont are either Abergavenny (about 14 miles away) or Hereford (about 15.5 miles away).

By Bus - Unfortunately, there are no bus services that run to and from Grosmont; therefore a taxi may be required.

From London - Trains run from London Paddington station to Abergavenny/Hereford. From these places a taxi will be required to Grosmont.

Return To The Start - The Three Castles Walk is a circular tour beginning and ending in Grosmont.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.

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