Classic Dorset Short Break

5 Days & 4 Nights 4.7 Read 3 reviews
  • A short break discovering quintessentially English landscapes in Dorset.
  • Historic and picture postcard hilltop town of Shaftesbury.
  • Walk the Thomas Hardy Trail to Higher Bockhampton, his birthplace.
  • Reputed fertility symbol and ancient giant hill figure of Cerne Abbas.
  • Superior accommodation in charming local inns and guest houses.
Take a long weekend to explore these classic and quintessentially English Dorset landscapes, staying in charming and high quality inns and guesthouses. Immerse yourself in this varied countryside of sweeping down lands, green and rolling hills, pretty stone villages and bluebell bedecked woodlands. Drink local brews in cosy pubs by the fire. Visit places associated with Hardy, such as Higher Bockhampton, where he was born, Shaftesbury, the remarkable hill top town that he referred to as “Shaston” in his novels., and Dorchester, a bustling market town and Hardy’s fictional “Casterbridge”.
Easily accessible from London or other gateways this short break takes you through the rustic and idyllic landscapes of Dorset. Walk through quintessentially English countryside with hidden villages and cosy pubs, whilst staying in superior and delightful guest houses and inns in interesting and historical towns.

Tour Style:

Self Guided | Go at your own pace on an independent tour.


Multi Center Walking | You will spend multiple nights in one or more of the locations on this walking tour

This trip is suitable for:

Multi-Generational, Mixed Abilities, First Timers

Activity Level & 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.


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.


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.

  • 4 Nights accommodation in superior guest houses & inns
  • 4 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
  • 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
  • Private transfers

When To Go

You can start your Classic Dorset Short Break tour anytime between March and October. You can start your on any day of the week during the season.

We offer this tour in spring, summer and autumn. Temperatures will probably be at their best in the summer with long, sunny days. The climate in spring and autumn is mild with some great sunny days mixed with cooler and wetter weather. In spring you can enjoy the sights of spring flowers in bloom and autumn offers beautiful colours and sun-warmed heaths.

Getting to the Start

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 the End

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.

Luggage 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.

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.

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.

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Day 1 Arrive in Shaftesbury and overnight Day 2 Shaftesbury Loop via Wessex Ridgeway 9 miles / 14.5 km Day 3 Transfer to Cerne Abbas Giant, explore then walk to Dorchester 8 miles / 12.9 km Day 4 Transfer to Bere Regis, walk to Dorchester via the Hardy Trail 13 miles / 20.9 km Day 5 Onward travel

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