Self Guided Walking Holidays & Cycling Holidays

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Dramatic skies above the village of Cerne Abbas


  • 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”.

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 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 4: 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

Overnight: Dorchester

Day 5: 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 in superior and charming 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 Classic Dorset Short Break 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 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.

Grade & Terrain

This tour is graded as easy to moderate. You will be walking trough a diverse variety of landscapes; down lands, heaths, wooded, riverside trails, and through farmland. Some of the time you will be walking on named trails, such as the Wessex Ridgeway, and the Hardy Trail. 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.


  • 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 (transfer to Shaftesbury included)
  • 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
  • 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.

Great hikes, great places


This was my first time taking a walking adventure like this, and I went with a group. We had a great time overall--great views, great trips, great accommodations. Our first ramble we used the app exclusively, and it works excellently. Thereafter we tried following the directions, and found there are a few places they could be improved or updated, leading us to fall back on the app to make sure we didn't get lost. Highly recommend using both. We also thought that the final walk of the tour probably shouldn't be the longest, and ended up cutting ours shorter. (there are some good and easy ways to cut it down to half or three-quarters, depending on how you're feeling) Bottom line, be prepared, have a map with you, and have fun.


Vermont, USA


Beautiful Countryside


A group of 4, we are three college friends now in our late 40s, and a fiancé in his mid 30s. We did the 3 days of walking April 22-24, hoping for flowers, flowering trees, and lambs, and that's what we got. The accommodations were superb. Breakfasts were tasty and filling. The restaurant at The Grosvenor Arms in Shaftesbury served fantastic food and libations in a charming atmosphere. We did not use any walking sticks, and never wished we'd had them. The first day was the Shaftesbury Loop, and the app marked it as 9.8 miles. It was an enjoyable walk all around. The sun was out and it was warm enough for short sleeves for most of the walk. We encountered an electric fence that had us puzzled, until one in the group saw a section covered in rubber, so we straddled it there and continued on. The second day we were dropped at Cerne Abbas Giant, and we set off on the 9-mile path to Dorchester. While there wasn't as much up and down on this trail, it seemed a bit more "difficult" in that the paths were more rugged, with sloped fields, lots of tussocks and bumps, as well as very muddy, mucky cowpaths. We were thankful for our waterproof boots. When we came to a another electric fence that was a single line, we crawled under it. This day was cooler and windier, so an extra overshirt was appreciated at times. A highlight of this walk was going through a rapeseed field in bloom. The worst part of this walk was many muddy cowpaths. The third day showed a strong chance of rain, so we had the driver drop us off in Puddletown instead of Bere Regis, which shortened the walk from 13.8 miles to 6. We are so glad we did that, as it did rain--a light gentle rain. That decision afforded us time to linger in interesting places, like the church in Puddletown and the Thomas Hardy Visitor Center, which serves food and drinks. A highlight was the Thorncombe Woods, rife with bluebells. Consider the shorter hike of 6 miles from Puddletown. It will probably save you a cab fare back.


Sarasota, FL, USA


Classic Dorset Short Break

5.0 2


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