Pennine Way Trail Holidays

The oldest and most iconic National Trail offers a rugged taste of Northern England – stretching from the Peak District to the Scottish Borders on a challenging but rewarding route of remarkable contrasts. Explore the Pennine Way for three days, a week or even longer. Find inspiration for your walking adventure using our suggested itineraries, or select one of our bookable itineraries which are highlighted with a star.

Find inspiration for your walking adventure using our suggested itineraries below, or search for a walking holiday company to help plan your dream trip.

Short Walks & Breaks

Three-to five-day adventures based along sections of the trails that pack in a bit of everything: great hikes plus hands-on experiences, impressive sites, fabulous food and drink and amazing places to stay.

Calderdale Class: Funky Towns, Literary Legends & Wild Hills around Hebden Bridge

Spend five days discovering the charms of Hebden Bridge and exploring the dramatic landscapes and rich heritage of the Calder…

8 KM

Heriol

Wedi’i arwyddo’n glir

Peaks Power: Hiking, History and High Adventure in Britain’s Original National Park

Plan a three-day escape to the Peak District, walking the start of the Pennine Way and discovering Derbyshire’s rich heritage…

12 KM

Esmwyth

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Roof of England: High Roaming, Rich Heritage and Dark Skies in the North Pennines

Spend five days exploring the fells, moors, mines, riverbanks and Roman ruins around Alston, the country’s highest market town

10 KM

Cymedrol

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The Great North Road: A Motorhome Adventure

If you love exploring new destinations in your motorhome, you'll love this stunning 9-day route through Northern England.

10 KM

Esmwyth

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Pennine Way Short Break: Hiking and Heritage Around Hebden Bridge

Base yourself in the quirky and unconventional Calderdale town for a few days of excellent walking, eating and exploring

10 KM

Cymedrol

Wedi’i arwyddo’n glir

Longer Walks & Escapes

Discover the length and breadth of these impressive trails with walks for all abilities, always accompanied by stunning views and a comfortable place to stay.