Dorset & Wessex Trails

Dorset & Wessex Trails

Trip Highlights

  • Far from the Madding Crowd
  • Walking the Coast and Hills of Dorset
  • Historic Town of Dorchester
  • Natural Wonders of Durdle Door and Lulworth Cove

Trip Summary

From Lyme Regis to West Lulworth, parts of this walk are as beautiful as it gets in the British Isles. Yet you are in no wilderness area being fairly near attractive villages and towns throughout the journey. This is a walk of great variety, naturally concentrating on the popular Dorset Coast Path. The Dorset coastline is an area of outstanding geological importance as over 200 million years of rocks have been laid down, bent and twisted before being eroded by the sea to expose rock profiles on beaches, accessible to fossil hunters and scientists. So important is this area that it is now a UNESCO World Heritage Site. However our walk also dips inland to visit a mysterious region of ancient hill forts, Roman and Saxon remains – the ancient kingdom of Wessex. You have a couple of nights in Dorchester, Thomas Hardy’s Casterbridge, with its beautiful museum and essentially Roman form. Here there are walking options within the town, or without, to the beautiful village of Cerne Abbas and out to find Hardy’s cottage in the woods. The tour starts from another town with literary associations: Lyme Regis with its medieval Cobb (harbour wall), which is a favorite place for almost everyone who visits it. John Fowle’s novel “The French Lieutenant’s Woman” is set there and the author lived in the town until his death in 2005. On the walk you also visit Abbotsbury a gem among English villages, while Maiden Castle and the Cerne Giant are spectacular archaeological sites of great importance. The last part of the walk roller coasters along the cliffs above the natural arch formation of Durdle Door and then down to Lulworth Cove – a perfect oval cove protected from the sea by rocky fingerlike peninsulas. The coastal villages can be rather crowded in high summer and are understandably popular, but you will also find many quiet areas whilst walking. The weather is generally warmer and more settled on England’s south coast than in other parts of Britain and some steep paths aside, the grade is on the easier side of our walking holidays in the UK.


Easy to moderate. There are some steep sections of coastal path that can sometimes be avoided, however the steep hills are a maximum of 200 metres of ascent/descent in one go and are often much less.


Make your way to Lyme Regis. Explore the town and in particular the medieval stone (Cobb) harbour. The Lyme Regis museum is a great introduction and insight into the natural history of the area. Accommodation: Two nights are spent in a 4 star guesthouse.

Meals:  Nil

Walk through the famous under-cliff, a nature reserve on the coast west of town to Axemouth and Seaton in Devon and return to Lyme Regis by bus or explore coastal cliffs for fossils.

Meals:  B

Today is a beautiful roller coaster walk with fascinating features such as Golden Cap 191m, the highest point on the South Coast, an interesting pub at Seatown which was heavily involved in smuggling and some nice clifftop trails. Accommodation: West Bay, the harbour of the old market town of Bridport. We use a number of guesthouses.

Meals:  B

This is a charming walk which takes you off the cliffs and along the first part of the pebbly long shore drift which eventually becomes Chesil Beach, the longest shingle beach in Europe. At West Bexington you climb steeply inland and then head off to the prehistoric fort of Abbotsbury Castle. You drop down to Abbotsbury, one of the most traditional villages in the UK. We recommend a stroll up to St. Catherine’s chapel at sunset or dawn. This chapel served as a lighthouse from monastic times and through the destruction of the monasteries as a reference landmark for shipping. Accommodation: A number of accommodation is used in the village.

Meals:  B

Inland via Dorset Ridgeway path to Maiden Castle, a large ancient earthwork fortress sacked by the Romans in the 1st century A.D. and Dorchester. Maiden Castle is the greatest Iron Age fort complex in the UK and takes almost an hour to walk round. Find the remains of the Roman temple, and look at the formidable ramparts. The Romans established Dorchester on the plain below the fort, and the existing town still exhibits a plan set within the lines of the Roman design that was not broken until the coming of the railways in the 1840s. There is also a Roman house you can visit. Accommodation: Your accommodation is an early 19th century town house that has been converted into a 4 star guest house, offering spacious rooms and great comfort right in the heart of this busy town.

Meals:  B

While your baggage goes direct from Dorchester to West Lulworth, you return by bus or by train to the coast at the lively resort of Weymouth, take a local bus to Bowleaze and then follow the Dorset Coast Path eastwards along the brilliant white chalk cliffs from Weymouth to Lulworth Cove. On the way you pass the natural arches of Bats Head, Durdle Door and the long abandoned medieval village of Ringstead. This is another roller coaster day, but you can bypass the hilliest sections with a more inland route. Lulworth Cove is a beautiful spot, albeit a busy tourist honeypot. However most visitors do not stay the night and you could get up before breakfast to have the cove all to yourself or return to Durdle Door in the evening for beautiful sunsets! Please note West Lulworth has a 2 night stay minimum over weekends. If you have a Saturday or Sunday trip departure date, you would be in West Lulworth over the weekend. You can I) Have 3 nights in Dorchester (Nights 5-7) II) Add a post night in West Lulworth, to stay on night 7 and an extra night 8. Accommodation: 4 star B&B/Guesthouse

Meals:  B

Trip concludes after breakfast

Meals:  B

What's Included

  • 7 breakfasts
  • 7 nights accommodation in small hotels and guesthouses on a twin share basis with ensuite facilities where available.
  • One piece of luggage per person transferred from Inn to Inn, not exceeding 20kg. Please note all luggage moves over October dates will incur a Winter Transfer Supplement
  • Full route notes and map package.
  • Emergency hotline

What's Not Included

  • Lunch, Dinner and drinks
  • Entrance fees
  • Travel insurance
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls
  • Unscheduled transfers required during the trip

Upcoming Travel Dates


Great service in planning the trip and wonderful choice of routes and accommodation

C. Vardy, British Columbia, Canada, 20 Sep 2019

I will definitely use Sherpa for future hiking adventures. The route we selected was beautiful. B&Bs Sherpa selected were fantastic. Cozy, friendly, great locations to explore the towns and fantastic breakfast menu. Suggested side trips were fun. Notes on attractions were informative and made us look forward to the sites.

N Burkholder, Wisconsin, USA, 19 Sep 2019

Baggage transfer was first rate. Accommodations all had personal washrooms and the locations were great. Awesome trails; some a little more vigorous than anticipated but wonderful.

P. Arsenault, New Brunswick, Canada, 05 Sep 2019

Very memorable trip and would go again.

C. Bates, Missouri, USA, 22 Jul 2019

The B&B's that you arranged had very nice and helpful hosts….. It was a great vacation. The scenery was terrific. We've done seven long distance hikes in the U.K. and we appreciate the work that you and your team put in to make this one special.

J Painter, New York, USA, 25 Oct 2018

All of the properties were very good. The highlights of the tour were Abbotsbury, the options for walks around Dorchester and the walk to Hardy’s cottage

C Kerlin, Lopez Island, Western Australia, 05 May 2018


Duration:8 Days
Starting Point:Lyme Regis
Finishing Point:West Lulworth
Activities:Self-Guided Walking
Grade:introductory to moderate  Click for more information
Trip Code:WDC
Prices From:GBP£810 Per Person
2021 Single Supplement:GBP£270  Click for more information
2021 Solo Traveller:GBP£300  Click for more information
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.