Self-guided walking holidays
From long-distance trails with luggage transfers to relaxed, single-centre breaks, we create self-guided walking holidays that can be shaped around your time, interests and pace.
Tailored Holidays
We adapt routes, timings and pace to create the right challenge for you
Local Knowledge
Routes, places and experiences chosen
by local specialists
Private Transfers
Your own car and driver - no buses or groups so the day goes at your pace
Private Guides
Private guide available on request to help you find your feet
Dorset is one of England’s finest walking destinations, with its dramatic World Heritage coastline, rolling chalk downlands, peaceful valleys and historic villages. But what makes a Henderson’s Dorset walking holiday special is the flexibility and personal service we offer.
Our long-distance routes can be adapted into shorter holidays of as many days as you like, so your trip fits your pace and schedule and your route each day can be adapted to suit your abilities. And private transfers means that you won't be having to find bus-stops and fit to fixed schedules.
For walkers who would like extra support, we can sometimes offer a private guide, whether for the first day or two while you find your stride or for the whole journey. Just tell us which walk and dates you have in mind and we will do our best to make it happen.
Bringing your four-legged friend? We have dog-friendly accommodation and routes as well.
Our selection of perfect self-guided Dorset walking holidays
Hambledon Hill Ironage fort
Ancient Dorset: Hillforts & Ridgeways
Named as one of The Telegraph's top ten "Best UK walking holidays for 2026", this self-guided, inn-to-inn walk with luggage transfers follows ancient ridgeway tracks, over Iron Age hillforts and chalk downlands, rich with wild flowers and butterflies.
Long Distance
3 - 8
Breakfasts
Picnics
3-4
Knoll Beach Studland
Walking Dorset's Jurassic Coast
For travellers seeking a self-guided walking holiday on the Jurassic Coast, we provide locally designed itineraries, accommodation and expert on-the-ground support. This self-guided, inn-to-inn walk takes you along Dorset's iconic Jurassic Coast, the only natural UNESCO World Heritage site in Britain. Expect stiff climbs, spectacular scenery, quiet coves and bustling seaside towns.
Long Distance
3 - 9
Breakfasts
Picnics
5
Bluebell woods in Dorset
Heart of Dorset Walking Weekend
The perfect spring weekend walking break, staying at the wonderful New Inn in Cerne Abbas, set in a peaceful valley amongst the chalk downlands of central Dorset. Visit the mighty Cerne Giant as well as ranging further afield over flower-filled hillsides with larks singing overhead.
Weekend Break
2 - 3
Breakfasts
Picnics
2
A Weekend in Hardy Country
A three day walking break, staying in the historic King's Arms in Dorchester where Hardy wrote much of The Mayor of Casterbridge. The perfect base to explore his homes and ramble around the countryside which informed his writing.
Weekend Break
3 - 5
Breakfast every day
1
Rural Rambles
Spend a weekend in a cosy inn with fabulous food and work up an appetite walking the quiet paths and byways of the county. Away from the tourist trail you'll find quiet picturesque villages, ancient ridgeway tracks and abundant wild flowers.
One Centre
3
Breakfasts
Picnics
3
Iconic Dorset Walks
A self-guided walking weekend taking in the best bits of the county for walking, including the Jurassic Coast, the Purbeck ridgeways and the Rude Man of Cerne.
Weekend Break
3
Breakfasts
3 picnics
3-5
To The Sea!
A week of self-guided walks which all take in some of the coast but also venture further inland to visit some interesting and quieter parts of Dorset.
One Centre
7
Breakfasts
6 picnics
5
Walking Hardy's Dorset
A series of six fairly easy, self-guided day walks exploring the Dorset of Thomas Hardy and taking in some of the places which inspired his works including his homes and the peaceful church where his heart lies buried.
One Centre
7
Breakfasts
5 picnics
1
South West Coast Path
This trail covers the length of the Dorset's Jurassic Coast, the only natural UNESCO World Heritage site in Britain. Walking from West to East, this route is the final leg of the South West Coast Path. The same as our Jurassic trail, but the other way round! Expect stiff climbs, spectacular scenery, quiet coves and bustling seaside towns.
Long Distance
3 - 9
Breakfasts & picnics
5
Dorset Oddities
Spend a week exploring some of the stranger bits of the county including an abandoned village, The Rude Man of Cerne, Hell Lane and The Hell Stone, an island where you can't mention rabbits and a rock thrown by the devil himself.
Once Centre
3 - 9
Breakfasts
6 picnics
1
