Self-Guided Walking Tours & Biking Tours

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Gold Hill in the historic town of Shaftesbury


  • Discover the quintessentially English landscapes of Thomas Hardy’s Dorset.
  • The chalk downs of Cranborne Chase, an Area of Outstanding Natural Beauty.
  • Walk the Thomas Hardy Trail to Higher Bockhampton, his birthplace.
  • Historic and picture postcard hilltop town of Shaftesbury.
  • Overnight stays in charismatic and charming local inns and guest houses.

Explore the rural idyll of Thomas Hardy’s Dorset staying in charming and characterful inns and guesthouses. These are the classic English landscapes of Hardy’s “Wessex” which appeared throughout his novels and gave him inspiration.

Picture yourself walking through varied countryside of sweeping down lands, green and rolling hills, pretty stone villages and bluebell bedecked woodlands. Visit places associated with Hardy, such as Higher Bockhampton, where he was born, and Shaftesbury, the remarkable hill top town that he referred to as “Shaston” in his novels.

Follow trails to the ancient giant naked chalk figure of Cerne Abbas, up to Win Green, the highest point in Cranborne Chase, with views as far as Glastonbury Tor, and along the spectacular shoreline near the harbour town of Weymouth.

Day 1: Arrive Shaftesbury & overnight

The hilltop town of Shaftesbury makes you feel like you have arrived on a film set. It is the site of the former Shaftesbury Abbey founded in 888 by King Alfred. From Gold Hill on a fine day you can see all the way to Glastonbury Tor and over quintessentially English countryside. In some of his novels Hardy referred to this town as “Shaston”.

A transfer from Gillingham Train Station brings you to your charming accommodation.

Overnight: Shaftesbury

Day 2: Shaftesbury Loop via Wessex Ridgeway

Make your way out of Shaftesbury along its attractive and quaint streets and head into the rolling green countryside, joining up with the Wessex Ridgeway.

The Anglo-Saxons referred to southern England as “Wessex” and Hardy also referred to this area in the same way in his novels.  The trail takes you to the pretty villages of Donhead St Mary and Donhead St Andrew. Perhaps stop along the way for a pub lunch and a locally brewed beer before making your way back to Shaftesbury past pretty ponds and woods.

Walk: 9 miles

Overnight: Shaftesbury

Day 3: Transfer to Cranborne Chase, walk to Shaftesbury via Win Green Viewpoint

Cranborn Chase is an Area of Outstanding Natural Beauty and located just over the border into the county of Wiltshire. This morning a short transfer brings you to Tollard Royal, a village central within these glorious landscapes. From here follow the Wessex Ridgeway Trail north.

En route climb up to Win Green Hill which is the highest point in Cranborne Chase and provides panoramic views from the Isle of Wight and Purbeck Hills to Blackmore Vale and Salisbury Plain. Win Green is crowned by beech trees growing on a Bronze Age bowl barrow and the Ox-drove links the countryside of Thomas Hardy's novels with Salisbury. This was a long distance droving route along which cattle were herded from Devon and Somerset to the Hampshire ports.

Walk: 9 miles

Overnight: Shaftesbury

Day 4: Transfer to Cerne Abbas Giant, explore then walk to Dorchester

After a hearty breakfast a transfer brings you to the Cerne Abbas Giant, an ancient naked figure carved into the chalk hillside. Standing at 180ft tall, this is Britain's largest chalk hill figure. Local folklore has long held it to be an aid to fertility. Spend time exploring here before wandering through the lovely village of Cerne Abbas, which grew around its Benedictine Abbey (AD 987).

From Cerne Abbas head south, mostly walking close to the Cerne River and then crossing the Frome River before arriving into the centre of Dorchester.

Walk: 8 miles

Overnight: Dorchester

Day 5: Free day in Dorchester

Dorchester is a bustling market town and also Hardy’s fictional “Casterbridge”. Recommended is the Dorset County Museum, which has a comprehensive Hardy Exhibition and includes a reconstruction of Hardy's study. Also explore Max Gate, now a National Trust property and Hardy’s sophisticated town house.

There are also many other intriguing sights to see here, such as the Town Pump, Borough Gardens or the excavations of a Roman Town House.

Overnight: Dorchester

Day 6: Transfer to Bere Regis, walk to Dorchester via the Hardy Trail

Today walk in Thomas Hardy’s footsteps. A short transfer brings you to Bere Regis where you link up with the Hardy Trail which takes in towns and villages from his stories, and the green and pleasant landscape of the county of Dorset, so beautifully portrayed in his written word.

In the village of Higher Bockhampton is Hardy’s Cottage, where he was born in 1840. A cob and thatch house built by his grandfather, it was here where he wrote some of his early short stories, poetries and novels, such as “Far from the Madding Crowd”.  After this visit divert off the Hardy Trail and cross the River Frome before arriving back in Dorchester.

Walk: 13 miles (with shorter options available)

Overnight: Dorchester

Day 7: Walk to Weymouth via Jubilee Trail, South Dorset Ridgeway & South West Coast Path

Walk out of Dorchester straight from your hotel and link up with the Jubilee Trail which brings you though quiet villages, passing rural churches and offering extensive views of rolling downs and secret valleys which make Dorset so special. Then walk for a while along the South Dorset Ridgeway and en route view the Osmington White Horse, the only chalk hill figure in England that has both a horse and a rider.

Continue along the beautiful coast line into the bustling and immense harbour of Weymouth, where Hardy lived and worked. The train back to Dorchester takes only 15 minutes, so feel free to spend the evening here if you wish.

Walk: 13 miles

Overnight: Dorchester

Day 8: Onward travel

Make your way from Dorchester to other major gateways in order to make your onward journeys.


On this tour you will stay in charming small hotels, guest houses and inns, centrally located in historic towns.

Single Rooms & Solo Walkers

If you require single rooms we would be happy to accommodate you although there is a single room supplement payable.

We also welcome solo walkers on this tour, again a supplement is payable.


Breakfast is included each morning. Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will be more than happy to provide a packed lunch on request and this can be booked on arrival. Dinner is available either at your accommodation or in nearby pubs or restaurants.

We regularly use the following properties but may accommodate you elsewhere if these are not available.




The Grosvenor Arms - Shaftesbury

You will be warmly welcomed at The Grosvenor Arms, which has been an inn since medieval times and is located in the centre of Shaftesbury. There are 16 comfortable rooms with traditional, yet stylish decor in which you can relax.







The Casterbridge - Dorchester

The Casterbridge - Dorchester

Conveniently located in the centre of Dorchester, this handsome wisteria clad Georgian House is a charming place to stay with free Wifi, a comfortable and relaxed ambience and superb breakfasts.





You can start your Thomas Hardy's Dorset tour anytime between March and October.  You can start your on any day of the week during the season.

Time of Year

We offer this tour in the spring, summer and autumn. The climate in spring and autumn is mild with some great sunny days mixed with cooler and wetter weather. Advantages in the spring are the beautiful spring flowers in bloom. Temperatures will probably be at their best in the summer and in the Autumn/Fall it there will be nice colours and sun-warmed heaths.

Grade & Terrain

This tour is graded as easy to moderate. You will be walking through a diverse variety of landscapes; down lands, heaths, wooded, coastal and riverside trails, and through farmland. Some of the time you will be walking on named trails, such as the Wessex Ridgeway, Jubilee Trail, Hardy Trail and the South West Coast Path. But you will also be walking on unofficial trails and so you will need to be vigilant. You will need to have good physical fitness to fully enjoy this tour as, at times, there are some elevation gains and losses to negotiate.

Navigation, Route Notes & Maps

When walking on “official trails” it will be quite well way marked and relatively easy to follow. However, you will also be walking on trails through countryside that are either not waymarked at all or intermittently. Therefore you will need to be vigilant and follow your detailed routes notes. GPS data will be provided for you via the Macs Adventure App. Further information will be provided upon receipt of your booking.

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care

General Information

The distances and ascents/descents are approximations of the recommended routes.Please be prepared by packing all necessary items, for example. proper rain gear, sun hat, sunscreen. Your information pack has detailed advice and a kit list on what to take.This includes good waterproof gear, walking shoes/boots, and lots of other useful bits and bobs.

Getting to Shaftesbury

From Gillingham Train Station to Shaftesbury there is an included transfer to your hotel.  Gillingham, a town which is 15 minutes away from Shaftesbury, is on the main train line from London. It is a 2 hours direct train service. Therefore you can fly into any of the London Airports. For comprehensive information please visit the National Rail or Trainline websites.

Getting from Dorchester

The closest airport to Dorchester is Southampton Airport, which has flights from Glasgow, Paris and Manchester, etc. There are hourly direct trains from Southampton Airport Parkway Station to Dorchester South Train Station. There is also a direct train line service from London, taking approx. 3H. There are two train stations in Dorchester, West and South, but the majority of trains from London come into Dorchester West.

Visit the National Rail and Trainline websites for more information.


  • 7 Nights accommodation in superior guest houses inns
  • 7 Breakfasts
  • Luggage transfers
  • People transfers where mentioned
  • Detailed information pack, route notes and maps
  • 24/7 telephone support from our UK office


  • Travel insurance (required)
  • Travel to Gillingham
  • Travel from Dorchester
  • Train fare Weymouth to Dorchester
  • Lunches & Dinners
  • Drinks and snacks
  • Taxi transfers or public transport should you need to skip a stage
  • Personal equipment


  • Additional nights before, during or after the walk
  • Single Room Supplement(s)
  • Solo Traveller Supplement
  • Private transfers

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as the these towns and especially Shaftesbury can get very busy especially during July and August. You will find up to date availability on our website.

How fit do I need to be?

You will need to have good physical fitness to fully enjoy this tour as, at times, there are some elevation gains and losses to negotiate.

How do the baggage transfers work?

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

What equipment do I need?

Your detailed information pack will be sent to you after you book. This has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes and a day pack.

When is the best time of year?

The best months for walking in the spring, summer and autumn when the weather is fair. Spring is great as the wild flowers will be in bloom and the Autumn when it is a bit quieter.

What happens if I can’t walk a stage?

You can use public transport or a local taxi to continue to your next overnight stop.

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