Self-guided Dorset walking holidays
Is there a better place in England for walking? With its magnificent World Heritage coast, chalk downlands, peaceful valleys and historic villages, Dorset has everything you could wish for. We offer a range of walking holidays - long distance trails with baggage transfers, single centre multi-day holidays and some guided day walks. All long-distance walks can be broken down into shorter breaks of as many days as you would like. Or we will happily mix and match walking with tours and sight-seeing to create your own perfect Dorset escape.
We are sometimes be able to offer our walking holidays with a private guide, either for the first day or two until you are acclimatised or for the full walk. Just let us know which walk and dates you are looking at and we'll see what we can do.
Our selection of perfect self-guided Dorset walking holidays
Knoll Beach Studland
Walking Dorset's Jurassic Coast
A self-guided, inn-to-inn walk 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
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 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
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
Walking The Best of Dorset
A seven night, one-centre holiday (you don't move accommodation every day) showcasing the best walking in the county, taking in the iconic Jurassic Coast, iron age hillforts, peaceful valleys and high chalk downlands.
One Centre
3 - 7
Breakfast every day
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
