Pennine Way Walking Holidays

The Pennine Way, the UK’s most iconic National Trail, offers rugged beauty, remote landscapes, and challenging terrain along its journey through the spine of Northern England from Derbyshire to the Scottish Borders. Celebrating 60 years in 2025, it showcases dramatic moorlands, rolling hills, and landmarks like Hadrian’s Wall—perfect for adventurers seeking Britain’s ultimate walking challenge and unforgettable scenery.

Nights
5 to 23 Nights
Distance
68 to 270.5 miles
Location
England
Difficulty
Moderate – Challenging
Season
Apr to Oct
Price from
£685

Highlights

Unforgettable scenery, remote landscapes, and a challenging adventure along the UK's first National Trail.

Traverse the Peak District, the Yorkshire Dales, and the Northumberland National Park.
Wonderful stretch of Hadrian's Wall Path
Kinder Scout
Home to the famous mass trespass and the trail’s dramatic start.
Malham Cove
A striking limestone amphitheatre with breath-taking views.
High Force
One of England’s most spectacular waterfalls.
Walk in areas of true wilderness.
From £685 per person
Book

Why Walk the Pennine Way?

Walking the Pennine Way is a once-in-a-lifetime adventure that immerses you in some of the UK’s most iconic and diverse landscapes. Spanning 268 miles, this trail offers a rich tapestry of experiences, from the rugged moorlands of the Peak District to the serene beauty of the Scottish Borders. The route demands a high level of physical fitness and is best suited to experienced long-distance walkers who relish a challenge. Along the way, you’ll encounter breath-taking scenery—think dramatic cliffs, cascading waterfalls, and rolling farmland—and traverse historic routes, including Roman roads and Hadrian’s Wall. Beyond its physical demands, the Pennine Way offers moments of deep solitude, connection with nature, and encounters with abundant wildlife. Add to this the charm of picturesque villages and the warmth of local hospitality, and the Pennine Way becomes not just a walk, but an unforgettable journey that rewards every step.

Why Walk the Pennine Way?

Path Walkthrough

The Pennine Way begins with a dramatic introduction, featuring steep climbs and exhilarating descents over the rugged moorlands and reservoirs of the Peak District. Early highlights include Kinder Downfall, sandstone ridges, and sweeping views from Black Hill. As you journey northward, you’ll traverse iconic landmarks such as Stoodley Pike, Malham Cove, and the glacial valley of High Cup Nick. The route transitions from gritstone and moorlands to the limestone landscapes of the Yorkshire Dales, offering unforgettable sights like High Force waterfall and the remote expanses of Cross Fell, the trail’s highest point. Further along, the trail intersects with Hadrian’s Wall, providing a glimpse into Roman Britain, before weaving through quiet forests and valleys. The final stretch takes you over the dramatic Cheviot Hills, ending in the tranquil village of Kirk Yetholm—a fitting conclusion to an extraordinary exploration of England’s most celebrated trail.

Path Walkthrough

What Makes This Walk Unique?

The Pennine Way is more than a long-distance trail—it’s a journey through time, nature, and culture. Its ever-changing landscapes, from the windswept moors of the Peak District to the rolling hills of the Borders, are unlike anything else in the UK. The sense of remoteness and solitude is unparalleled, allowing walkers to connect deeply with nature and experience the serenity of vast open spaces. The trail is steeped in history, with ancient packhorse routes, Roman roads, and Hadrian’s Wall weaving a narrative of past centuries. Wildlife thrives here too, with sightings of curlews, red grouse, and wild hares adding to the magic. What sets the Pennine Way apart is the sheer variety of experiences it offers: each day brings new challenges, unforgettable vistas, and a sense of accomplishment. For those seeking both adventure and tranquillity, the Pennine Way delivers a truly unique walking experience.

Pennine Way Windy Gyle

Choose Your Walk

Our Pennine Way Itineraries

Edale to Kirk Yetholm

270 miles (434.5 km)

Edale to Horton-in-Ribblesdale

94 miles (151.3 km)

Horton-in-Ribblesdale to Greenhead

108 miles (173.8 km)

Greenhead to Kirk Yetholm

68 miles (109.4 km)

Key Information

  • Good standard accommodation at a mixture of guesthouses, farmhouses, local inns and B&Bs with en-suite or private facilities wherever possible
  • Breakfast
  • Luggage transfers
  • Personal transfer between accommodation and path that form a part of our standard package
  • Route planning
  • Walk pack including Trail Guide and mapping, itinerary, accommodation directions and route notes, lunch and dinner information, restaurant recommendations and holiday planning details

Customise your trip?

Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs.

Hand-Picked Accommodation: Comfort Along the Way

We seek out the best accommodation of its type available

Hand-Picked Accommodation: Comfort Along the Way

Media Gallery

Customise your trip?

Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs.

Not For You?

Explore one of our other holidays...

Walkers descending towards a mountain lake in the Lake District on the Coast to Coast Walk
Offa's Dyke Path

Offa's Dyke Path

Welsh Border