Quality guided and self-guided walking holidays along Hadrians Wall, Northumberland Coastal Path, Berwickshire Coastal Path, St Cuthberts, St Oswalds Way and lots more.

Your accommodation, luggage transfers, route map, guidebooks and our expertise is all included.

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Our holidays

Hadrian's Wall Trail

Both guided and self-guided holidays along this National Trail

St Oswald's Way

Self-guided walking holidays along both the full length and also the ‘highlights’ of St Oswald's Way

St Cuthbert's Way

Self-guided and guided walking holidays along St Cuthbert’s Way

Northumberland Coast Path

We offer a range of self-guided trips along the Northumberland Coast Path

Yorkshire Dales - Three Peaks

Three peaks in three days

Berwickshire Coastal Path

Dramatic clifftop scenery complete with arches, stacks and crumbling castles

Dales Way

Limestone pavements, through valleys, and alongside river banks

The Cumbria Way

Pass quaint villages, homely country pubs and fantastic scenery

Isle of Man

Spectacular clifftop views with much birdlife and contrasting sections on resort promenades

A Taste of Two Trails

Such varying trails that complement each other

Cleveland Way

Full Cleveland Way or Moorland/ Coastal sections for a shorter holiday

Herriot Way

Passes through some of the best and most varied scenery in the Yorkshire Dales

The Pennine Way

New for 2024 - The Pennine Way!

Northern Saints Trails

New For 2023

West Highland Way

Self-guided walking holiday along the full length of the West Highland Way

"We enjoyed our self guided Dales Way trip with Shepherds Way. Accommodation was comfortable though occasionally off track. Some hosts really went the extra mile for us by minding our bags or giving us a lift into town. The maps and guidebook were very useful The staff at shepherds way got back to us quickly for any queries."

Mary Randall
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Latest News

How Does a Self-Guided Walking Holiday Actually Work? Aug 2026


A self-guided walking holiday gives you a whole long-distance trail to yourself - no group, no guide, no logistics - while someone else books the beds, moves your bags and points you the right way. Here is exactly how it works. If you love the idea of walking a great British trail but the thought of booking a dozen B&Bs, working out daily distances and lugging a heavy pack has put you off, a self-guided holiday is almost certainly what you are looking for. It is the most popular way our guests walk with us, and once people have done one, most never go back to planning it all themselves. Here is what to expect. more...