Wessex Ancient Kingdom

Foot Trails signature Inn to Inn trail

This inn to inn (village to village) walking experience is your ultimate experience of hiking rural England. Full of history and breath-taking English countryside it can be 8 or 10 nights duration, spending two nights at each country inn on route.

From rivers to woods, character villages & cottages to breath-taking scenery & views, this trail has it all!

Discover England’s ancient Saxon kingdom, called Wessex. Begin in historic Wiltshire, before your trail takes you across the south of the county, into beautiful north Dorset and then on into Somerset.

For a Wessex Ancient Kingdom sample itinerary pop your details in the ‘Like to find our more?’ form.


Gold Hill in Shaftesbury

Custom made & crafted walking trips

Wessex Ancient Kingdom is a linear (one-way!) trail that leads from one country inn to another. Gain a sense of journey. You’ll spend two nights at each country inn and village on route.

Your Foot Trail will be custom made to suit your wishes and the English season you choose. Daily trails vary in lengths from 7 to 12 miles (12km to 20km) with some flexibility possible enabling you to lengthen or shorten your days.

8 and 10 night itineraries available. Luggage transfers are included with our trusted driver team.  Arrive by public transport (we will advise you of your nearest train station and help you transfer to your first country inn) or bring your car to the start (we can organise a transfer to collect your car at the end of your holiday).

Trail highlights include:

  • Castles, grand Manors, water mills and iron-age hill forts
  • Explore grand country estates and discover the stories of their interesting pasts
  • Follow ancient trackways to abandoned medieval villages
  • Step inside a medieval castle and look up at the Great Banqueting Hall
  • Soak up peaceful and atmospheric spots, relax
  • Be amazed by the beauty of Cranborne Chase, former royal hunting ground

To request a detailed 20 page mini brochure with example itinerary for this trip or ask questions – please use the form to your right >>

A view over ancient Wessex

Getting to South West England & Wiltshire

Getting here is easy, your trail usually begins near Warminster, Wiltshire or Tisbury, Wiltshire. Its about a 2 hour car journey from London, sub 1 hour from Bristol.

For a truly car-free option the nearest train station is at Warminster, Wiltshire or Tisbury, Wiltshire.(We will advise when your itinerary is confirmed)

For overseas guests the nearest airport is at Bristol or Southampton. London Heathrow is also easy to get to. Airport transfers can be arranged with a chauffeured car, just ask.

Wessex walking holiday accommodation

About the accommodations

One of the reasons guests choose Foot Trails is for our choice of authentic and quality accommodation.

Largely independently and privately owned, we enjoy a close and strong working partnership with all of our country inns. Small, personal and friendly with excellent hospitality, each country inn sits in an English village with comfortable bedrooms and delicious local food and produce including real ales and a selection of wines to enjoy with dinner after your walk.

On the Wessex Ancient Kingdom inn to inn trail you will enjoy a different country inn every two days, giving you the opportunity to explore where you are before moving on, build in rest days and of course enjoy the comfort of the inn.

Each country inn offers historic character, comfortable bedrooms, and an English village location. All bedrooms have en-suite bathrooms.

National Trust's Montactue House

Cost & availability

This tour is available starting any nights (subject to availability) as an 8 or 10 night itinerary. We strongly advise booking in advance as places are limited. The trail is best enjoyed between March & November.

Example budgeting quotes:

* From £1230 per person# for 8 nights
* From £1485 per person# for 10 nights

You will receive a fully detailed itinerary, confirmations of your accommodations and a price quote before you book. Once you confirm your booking your price will be guaranteed and no surcharges will be added.

#Based on two sharing en-suite accommodation, staying on a bed & breakfast basis. Includes all luggage transfers, accommodation & transport.


  • Foot Trails local knowledge and expertise working with you to create your custom made trip and itinerary
  • Personal Walk & Explore Box with everything you need – including
  • Local Ordnance Survey™ map exerts (waterproof) with your trails annotated
  • Trail guide cards (waterproof one for each day with easy to follow instructions)
  • Local stories and histories
  • Recommended lunchtime stops at country pubs and cafes
  • Nature cards for identifying wild flowers, trees & animals
  • Seasonal nature guide book
  • Sweets (for a boost on route)
  • Your en-suite accommodation
  • Breakfasts
  • One bottle of wine
  • Two decades of expertise and know-how
  • Inn to Inn luggage transfers with our trusted drivers
  • Drop off services when it makes a walk better
  • Help and support in getting ready for your trip

How to book?

Contact us with your preferred dates and we will look after the rest. You can call us on +44 (0) 1747 820626 or use the form on this page to send a message or request an itinerary.

From our guests –

“Here are the bits and pieces returned after the most fabulous holiday. It was perfect and fortunately for us the weather returned to sensible walking temperatures. We just wanted to ensure you were aware that all the arrangements for our holiday fitted together perfectly and we look forward to our next walking holiday with you.”
Martin and Jane

“We both loved our adventure prepared by you and David. So much so, that we want to go on another one this spring!”
Things we especially liked:
Good maps and instructions. The waterproof paper proved to be MOST important.
Fantastic accommodations and food. We loved every place we stayed. In fact, as the days went by they seemed to get better and better!
Beautiful terrain. We got some extraordinary photos and were surprised we NEVER saw another tourist!”
Peter and Nancy

Read our reviews on Trip Advisor 

English-Heritage's Old Wardour Castle

How do I find my way?

Trails are devised using our local knowledge and rigorously tested and checked. Find your way using either the easy to follow trail cards if you prefer not to map read, or the local Ordnance survey maps provided. Or a combination of both.

Where will I be walking?

Your walks are on public rights of way and a mixture of paths, tracks and trails through woodland, on farm land, village country lanes and countryside. Most walking is away from roads. Everything you need will be provided in your walk and explore pack.

To request a detailed 20 page mini brochure with example itinerary for this trip or ask questions – please use the form to your right >>

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