This self-guided 8-day hiking holiday explores the beautiful countryside of the Wiltshire/Dorset border in southern England. Start your journey in the historic cathedral city of Salisbury, following ancient Wessex paths through the region’s famous chalk hills and valleys. Pass neolithic monuments, idyllic country villages, and grand country houses before ending at the Saxon hill town of Shaftesbury.


  • Explore the medieval cathedral city of Salisbury
  • Walk ancient trails through the spectacular Dorset/Wiltshire countryside
  • Visit the historical sites of Stonehenge and Wardour Castle
  • Discover picturesque thatched villages and charming market towns
  • Enjoy sweeping views across the area’s famous chalk downs and valleys

Brief Itinerary

Day Highlights Overnight
Day 1 Salisbury Salisbury
Day 2 Salisbury to Amesbury Amesbury
Day 3 Amesbury to Great Wishford via Stonehenge Wishford
Day 4 Great Wishford to Broad Chalke via Wilton Bowerchalke
Day 5 Broad Chalke to Ludwell Donhead St Mary
Day 6 Ludwell to Farnham Farnham
Day 7 Farnham to Shaftesbury Shaftesbury
Day 8 Shaftesbury Shaftesbury

Detailed Itinerary

Day 1: Salisbury

Salisbury Cathedral and its famous spire.
Salisbury Cathedral and its famous spire.

Welcome to the medieval cathedral city of Salisbury. Once you’ve settled into your accommodation, take some time to explore. Start by touring the famed 13th-century Salisbury Cathedral, an imposing gothic structure with the tallest spire in the UK. Next door at the Chapter House, you’ll find an original 1215 copy of the Magna Carta. After a stroll around the city, head to the riverside for a relaxing evening at an idyllic waterfront pub.

Day 2: Salisbury to Amesbury

Views across the Wessex hills.
Views across the Wessex hills.

Your first day of walking starts just outside the city, with a visit to the historic remains of Old Sarum. This Iron Age hillfort was Salisbury’s earliest settlement before a new town was built on its present-day site in the 13th century. From here, you’ll set out into the delightful and secluded Woodford Valley. Fed by the clear waters of the River Avon, you’ll pass rolling fields, quaint villages, and grand country houses. Stop for refreshments at one of the numerous inns and pubs en route, before ending your day in the ancient town of Amesbury.

Walking distance: 12 miles (20 km)

Day 3: Amesbury to Great Wishford via Stonehenge

Woodhenge at the Stonehenge World Heritage Site.
Woodhenge at the Stonehenge World Heritage Site.

Today’s route takes you through Wiltshire’s unrivaled collection of prehistoric sites. Explore Stonehenge, Woodhenge, and the many other nearby neolithic monuments and barrows that dot the landscape. Continuing across open downland, you'll pass through the pretty thatched village of Stapleford to reach the Wylye Valley and your base for the night at Wishford

 Walking distance: 10-13 miles (17-21 km)

Plan your trip to England
Chat with a local specialist who can help organize your trip.

Day 4: Great Wishford to Broad Chalke via Wilton

Wilton House, Wiltshire.
Wilton House, Wiltshire.

Start day four with a short section on the Monarch's Way— the route taken by Charles II after his defeat at the Battle of Worcester in 1651. Here you’ll pass the ancient forest at Grovely Wood; if you’re visiting in spring, carpets of bluebells light up the woodland floor. After taking in sweeping views of Salisbury Cathedral, descend to Wilton, a lively market town founded in the 9th century. Tour the impressive Wilton House and its gardens, then hike a final stretch through Cranborne Chase before reaching the lovely village of Bowerchalke for the evening.

Walking distance: 10-13 miles (17-22 km)

Day 5: Broad Chalke to Ludwell

Ruins of Old Wardour Castle.
Ruins of Old Wardour Castle.

The first half of today's hike follows a historic ridge-top track (known as a drove) that links Salisbury and Shaftesbury. You’ll be rewarded with beautiful views from the chalk escarpment, and pass numerous prehistoric earthworks along the way. Descend the hills to reach the haunting ruins of Old Wardour Castle, used in the film Robin Hood: Prince of Thieves. Afterward,  follow the Wessex Ridgeway trail through typical English parkland and the secluded Nadder Valley, ending in the village of Donhead St Mary.

Walking distance: 10 miles (16 km)

Day 6: Ludwell to Farnham

Views across Cranborne Chase from Win Green.
Views across Cranborne Chase from Win Green.

Today you’ll climb steadily onto the hills to reach Win Green, the highest point in the area. On a clear day, stunning panoramic views reach as far as the Isle of Wight and Glastonbury Tor. Follow a ridge along another ox drove path until a gradual descent takes you to Tollard Royal, where you can visit the 19th century Larmer Tree Gardens and finish your day in the rural village of Farnham

Walking distance: 8 miles (14 km)

Day 7: Farnham to Shaftesbury

Golden Hill, Shaftesbury.
Golden Hill, Shaftesbury.

Day seven sees you walk the last stretch of your journey, heading back up onto the hills via the picture-perfect village of Ashmore. Cross the magnificent viewing point of Melbury Beacon, to arrive at your final destination: Shaftesbury. You'll enter the medieval hilltop town via its famous Gold Hill, a steep cobbled street lined with thatched cottages.

Walking distance: 11 miles (18 km)

Day 8: Shaftesbury

Views across Blackmore Vale.
Views across Blackmore Vale.

Your last day is free to explore historic Shaftesbury at your own pace. Stroll around the edge of the escarpment for great views over the surrounding hills and vales, visit Park Walk to see Blackmore Vale and the ruins of Shaftesbury Abbey, or relax and give your feet some well-earned rest.


Map of Walking Tour of Wessex: Salisbury, Stonehenge & Shaftesbury - 8 Days
Map of Walking Tour of Wessex: Salisbury, Stonehenge & Shaftesbury - 8 Days
Written by h h, updated Feb 18, 2021