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Walking Holidays

From long-distance trails with luggage transfers to relaxed, single-centre breaks, at Henderson's Dorset we create self-guided walking holidays that can be shaped around your time, interests and pace.

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.

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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 we can include private transfers so that you wouldn't be having to find bus stops or stick to fixed schedules.

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For walkers who would like extra support, we can offer a private guide, whether for the first day or two while you get into 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.

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Bringing your four-legged friend?  We have dog-friendly accommodation and routes as well.

Our selection of perfect self-guided Dorset walking holidays

Hikers on Bat Head looking towards the rock arch at Durdle Door

Gently Along The Jurassic Coast

Would you like to walk Dorset's Jurassic Coast without the challenging climbs and long miles? Henderson's Dorset has the perfect walk, visiting all the iconic sites of this beautiful coast but taking the easy route.

A accommodation

7 nights

A meals

Breakfasts & Picnics

A walking

Inn-to-Inn

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£1,505 pp

Hikers on Bat Head looking towards the rock arch at Durdle Door

Ancient Dorset: Hillforts & Ridgeways

In The Telegraph's top ten "Best UK walking holidays for 2026", this self-guided, inn-to-inn walk follows ancient ridgeway tracks, over Iron Age hillforts and chalk downlands, rich with wild flowers and butterflies.

A accommodation

8 nights

A meals

Breakfasts & picnics

A walking

Inn-to-Inn

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£1,550 pp

Hikers on Bat Head looking towards the rock arch at Durdle Door

South West Coast Path

Looking to walk the Dorset stretch of The South West Coast Path? Henderson's Dorset will book your accommodation and transfer your luggage, creating a stress-free walking holiday to remember.

A accommodation

9 nights

A meals

Breakfasts & picnics

A walking

Inn-to-Inn

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£1,665 pp

Hikers on Bat Head looking towards the rock arch at Durdle Door

The Wessex Ridgeway

Trace Dorset’s chalk ridgeway on this magnificent 62 mile trail, rambling along an ancient route and visiting historic sites and villages along the way.

A accommodation

7 nights

A meals

Breakfasts & picnics

A walking

Inn-to-Inn

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£1,190 pp

Hikers on Bat Head looking towards the rock arch at Durdle Door

Gently Along The Ridgeway

Explore The Wessex Ridgeway the easy way! This trail takes you high up along Dorset's chalk downlands, following an ancient route and visiting historic sites and villages along the way. Each day is designed to give you around five or six miles of walking and avoids nearly all of the climbs normally associated with this route.

A accommodation

7 nights

A meals

Breakfasts & picnics

A walking

Inn-to-Inn

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£1,190 pp

Hikers on Bat Head looking towards the rock arch at Durdle Door

Heart of Dorset Walking Weekend

The perfect weekend walking break! A comfortable inn and gentle walks over the mighty Cerne Giant as well as ranging further afield over flower-filled hillsides with larks singing overhead. Transfers from local stations are included to make your trip car-free.

A accommodation

2 nights

A meals

Breakfasts & picnics

A walking

One-Centre

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£375 pp

Hikers on Bat Head looking towards the rock arch at Durdle Door

Walking Dorset's Jurassic Coast

This self-guided, inn-to-inn walk takes you along the iconic Jurassic Coast, the only natural UNESCO World Heritage site in Britain. Expect stiff climbs, spectacular scenery, quiet coves and bustling seaside towns.

A accommodation

9 nights

A meals

Breakfasts & Picnics

A walking

Inn-to-Inn

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£1,665 pp

Hikers on Bat Head looking towards the rock arch at Durdle Door

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.

A accommodation

3 nights

A meals

Breakfasts & picnics

A walking

One-Centre

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£495 pp

Hikers on Bat Head looking towards the rock arch at Durdle Door

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.

A accommodation

7 nights

A meals

Breakfasts & picnics

A walking

One-Centre

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£1,290 pp

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