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At a Glance

Your Holiday at a Glance

Independent Walking Holiday
  • Wonders of Wessex Walk

Dates for 2023
  • 1 April - 31 October
  • 5 nights: From £530 per person based on 2 sharing
  • 6 nights: From £615
  • 7 nights: From £710
  • Loyalty scheme reduction applies for returning customers (see terms and conditions)
  • moderate grade walking holiday
  • 7 nights, 6 days independent walking between guest houses. 5 night and 6 night versions of this walking holiday also available
  • Visiting a number of exceptional historic sites such as Salisbury Cathedral, Stonehenge, Wilton House and Wardour Castle
  • Beautiful English landscape of chalk downland and valleys in the Cranborne Chase and West Wiltshire Area of Outstanding Natural Beauty
  • A unique and engaging walk which follows quiet paths to link the highlights of this part of southern Wessex
  • Historic and picturesque settlements such as Shaftesbury with quaint thatched cottages
  • Reasonably gentle walking following ancient routes along valleys and ridge tops on the Wiltshire / Dorset border
  • "(We enjoyed) the Wessex countryside and walking to Stonehenge, Old Sarum and through the burial mounds. Some of our favourite B&B's. Thanks for a memorable holiday." J & M. Krieger, USA
Accommodation and Meals
  • 7 nights B&B in a variety of small quality guest houses with ensuite accommodation. Mixture of inns or pubs, bed & breakfasts and small hotels. They are located in delightful historic properties. Lunches are picnic meals, often provided by your guest house. Evening meals are taken in your guest house or in local pubs and restaurants where you'll have a choice of local cuisine.
What's included
  1. 7 night's accommodation on a bed and breakfast basis
  2. 4 lunches
  3. Transport of luggage between guest houses
  4. Detailed walking maps and notes including information about the place through which you'll be walking
What's not included
  1. Transport to Salisbury and from Shaftesbury
  2. 2 lunches, all evening meals and drinks
  3. Entrance fees
  4. Travel insurance
  1. Take a look at our other walking holidays in southern England
  2. Take a look at all our independent walking holidays

Wessex Walks

This self guided walking holiday in southern England explores the beautiful countryside of the Wiltshire / Dorset border including the Cranborne Chase, a former medieval, royal hunting estate. Your walk starts in the historic city of Salisbury with its cathedral, a masterpiece of early English architecture, boasting the highest spire in the UK; and finishes at Shaftesbury, a Saxon hill top town with stunning views, lovely historic cottages and of course, the stunningly beautiful Gold Hill. In between, your walking trail follows secluded valley meadows with babbling streams and idyllic villages, as well as following ancient Wessex routes on rolling chalk downland offering marvellous far reaching views.

Each day you'll have a variety of interesting sites and experiences, as your walking trail meanders through some of the finest landscapes in southern England in the Wiltshire and Dorset hills. The most famous site is without doubt, the prehistoric stones at Stonehenge, which is at the centre of the most dense complex of Neolithic and Bronze age monuments in England, including several hundred burial mounds. Your walking holiday also passes through rich wildlife areas such as ancient forests, which in Spring are carpeted in bluebells and protected chalk downs with orchids. You'll also have the chance to visit the lovely house and grounds of Wilton House, the historic sites of Old Sarum and Wardour Castle, as well as a number of charming villages such as Ashmore and Tollard Royal.

Walking Profile

A moderate walking holiday with each day's walk averaging 17km or 10 miles with moderate ascents of about 120m at a time, with maximum daily ascent being 400m. The walk follows many different types of paths, tracks and small country lanes. Occasionaly the walking trail is steep when ascending or descending the chalk escarpments, but in general the walking is gentle in nature.


location map of wessex dorset wilts south Engalnd walking holiday UK

Day 1: Arrival

Welcome in guest house in cathedral city of Salisbury in Wiltshire. You may wish to arrive early in order to have more time explore this lovely city and visit the cathedral with the tallest spire in the UK. Extra nights at Salisbury are possible at the start of your independent walking holiday.

Day 2: Salisbury - Amesbury

Today's walk starts by visiting the earthworks and remains of Old Sarum. Located on a hill just outside of Salisbury, Old Sarum is the site of the ancient city, before a new city was built on its present day site in the 13th century. Afterwards you'll follow the delightful and secluded Woodford Valley with its small quaint villages and manor houses and the clear waters of the river Avon flowing through it. You can stop off at one of the numerous inns on route for refreshment before making your way to the town of Amesbury and your lovely guest house. 20km, +250m

5 night version of walking holiday goes direct to Broad Chalk, whilst 6 night version goes direct to Great Wishford

Day 3: Amesbury - Great Wishford via Stonehenge

Today you'll have the chance to visit a collection of prehistoric sites which are unrivalled in the UK. Visit the world famous stonehenge with its enigmatic stones, as well as other sites such as Woodhenge close by and a plethora of other mounds and earthworks. After walking across open downland you'll pass through the pretty village of Stapleford with its thatch cottages to reach the Wylye Valley. 17-21km, +300m

Day 4: Great Wishford - Broad Chalke via Wilton

Your walking route starts by following a short section of the Monarch's Way (a long distance trail which follows the route taken by Charles II after his defeat at the Battle of Worcester in 1651.) This path climbs onto a chalk down covered in ancient forest at Grovely wood; a great place to see carpets of bluebells in the Spring lighting up the forest floor. Your walking trail follows the edge of the chalk downs with great views of Salisbury Cathedral before descending to the pretty town of Wilton, the ancient capital of Wessex. Chance to visit the impressive Wilton House and its gardens, before crossing over the hills to reach the beautiful Ebble Valley in the Cranborne Chase - an ancient royal hunting estate. 17-22km, +300m. Shorter option available

Day 5: Broad Chalke - Ludwell

The first half of today's walk follows the ancient ridge top track (known as a drove) that linked Salisbury and Shaftesbury. Beautiful views from the chalk escarpment and numerous earthworks accompany your delightful trail. Afterwards you'll descend the downs to reach the haunting ruins of old Wardour Castle, used in the film Robin Hood: Prince of Theives. You'll then follow the Wessex Ridgeway trail through typical English Parkland and the secluded Nadder Valley to reach your accommodation at Ludwell. 16km, +300m

Day 6: Ludwell - Farnham

Your walking trail climbs steadily onto the hills to reach Win Green, the highest point in the area with stunning panoramic views which on clear days reach as far as the Isle of Wight and Glastonbury Tor. You'll follow a beautiful ridge top along an old Ox Drove before a gradual descent takes you to the pretty village of Tollard Royal hemmed in its valley bottom. Afterwards you have the opportunity to visit Larmer Tree Gardens, before the short walk to your next guest house. 13-14km, +210m

Day 7: Farnham - Shaftesbury

Your last day's walking takes you back up onto the hills via the pretty village of Ashmore. Lovely historic cottages surround a large pond set on the chalk plateau. Your walking route will then take you to Melbury Beacon, a great local viewing point before heading to the historic hill top town of Shaftesbury in Dorset. You'll enter the town by the famous Gold Hill with its steep cobbled street lined with thatched cottages. You'll be supplied with a walking route around the town to take all of the best views from the escarpment surrounding Shaftesbury. 18km, +380m

Day 8: Departure

Departure after breakfast


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For useful advice about independent walking and preparing for your self guided holiday please take a look at the articles in our top-tips section.

Once you have booked on this independent walking holiday in southern England, further information about the walking, the region and what to bring, will be sent to you. We do have a web page dedicated to what clothes and equipment you should bring. In addition, our travel shop has direct access to all the top walking and travel retailers. Please contact us if you need any further information.


Accommodation & Meals

7 nights B&B in a variety of small quality guest houses with ensuite accommodation. Mixture of inns or pubs, bed & breakfasts and small hotels. They are located in delightful historic properties, mainly in villages, but some in beautiful locations in the countryside. The B&B's are generally 4 star AA rated. Lunches are picnic meals, often provided by your guest house. Evening meals are taken in your guest house or in local pubs and restaurants. There will be plenty of local specialities to try and of course the local real ales. A couple examples of the types of guest house we use are shown below.

Name Type Details Rating  
Fairlawn House Guest House Fairlawn House is a fine Georgian Grade II listed town house offering a warm and friendly welcome and lovely food in the town of Amesbury  4 star rated enjoy England guest house in Amesbury wiltshire walking England UK
Travel Options

Travel Options

To Get to Salisbury

By Train

Salisbury is served by a main line train station. Routes from London are via Waterloo station and take about 1hr 30min.

By Air

There are 3 local airports with international flights: Bournemouth and Southampton are about 30 minutes drive away, whilst Bristol is about an hour away. The 3 London airports are between 1hr 30 and 2 hrs drive away.

By Bus

National Express operate services to Salisbury from cities throughout the UK including London. Advance ticketing is required.

More information on how to get to Salisbury can be found on the following website (external site): https://wikitravel.org/en/Salisbury_(England)

Return from Shaftesbury

There are regular bus services from Shaftesbury to Salisbury city Centre with Wilts and Dorset bus company. Bus lines 29, 26 and 27 run between the two towns providing about 6 services a day. The journey takes about 1hr 15min. More information can be found on the Wilts and Dorset website: https://morebus.co.uk/

Please visit our travel shop for links to useful sites for reserving airport parking or booking train tickets

Note: Please check concerning the availability of a holiday before booking any flights or trains. If you need further information or would like to discuss any aspect of your travel arrangements, please contact us, we’re here to help you.




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