Self-guided 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.
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 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 we can include private transfers so that you wouldn't be having to find bus stops or stick to fixed schedules.
For walkers who would like extra support, we can 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
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.
Short break
2 nights
