Click here to vote for Contours Holidays in the Wanderlust Reader Travel Awards!
Pennine Way

Pennine Way

An iconic walking trail through the Peak District, Pennines, Yorkshire and Northumberland.

3 to 22 nights
21-265 miles
Moderate to Strenuous

From £385 per person

Find your holiday

About the trail

Art of Stoodley Pike on the Pennine Way.The Pennine Way was Britain’s first ever National Trail, and it remains one of the best-known and arguably the most challenging of the lot. We offer holidays along its full 265-mile length, as well as some shorter options to make this monster of a trail fit busier schedules.

Through the wild landscapes of the Peaks, Pennines, Yorkshire Dales and the Cheviot Hills, the Pennine Way walking holiday straddles the spine of England as it stretches from Edale to Kirk Yetholm, taking in a wide variety of scenery from mountains to moorland. If you embark on the Pennine Way, expect to encounter inclement weather, phenomenal climbs and the binding comradery of walkers on a truly epic adventure.

We offer multiple holiday options along this trail. If you wish to experience the entire trail, simply select the first option from the list below.

Choose your route

  • Pennine Way
  • Pennine Way - Central Section
  • Pennine Way - South Section
  • Pennine Way - North Section
  • Pennine Way Short Break - North Section

About this route

3 nights
21 miles
Moderate
1st April to 20th October

From £385 per person

Pennine Way Short Break - North Section

Follow the River Tees through hay meadows bursting with wildflowers past a series of cascades that builds to the largest waterfall in England. The wild, empty moors of the North Pennines lie ahead, home to a variety of grouse, curlew, and hardy sheep.

This taste of the Pennine Way includes one of its best viewpoints: the glaciated chasm of High Cup Nick, which sweeps the gaze out over the mountains of the Lake District. From here, the walk descends to Dufton, nestled in the shadow of Cross Fell.

Available tours

Code Tour Duration Difficulty Price per person
PENSBN From Middleton-in-Teesdale to Dufton(T) 3 nights, 2 days walking Moderate £385

Short breaks

Code Tour Duration Difficulty Price per person
PENSBN From Middleton-in-Teesdale to Dufton(T) 3 nights, 2 days walking Moderate £385
Contours Walking Holidays Contours Cycling Holidays Contours Trail Running Holidays

Please be aware that this website uses cookies to give you the best possible experience. We value your privacy and treat your data with care. Learn more.

For more information, please refer to our privacy policy.

Strictly necessary cookies which are essential for navigating a website and using its features and functionalities. These temporary 'session' cookies are required for basic services such as logging in or making a booking.

Marketing cookies which are used to monitor our marketing & advertising efforts, enabling us to personalise content and enhance results.

Analytics cookies track website usage data, including traffic numbers, page views, and user interactions. This information helps us improve website performance and understand user behavior.

User experience cookies enhance the browsing experience by enabling features like heatmapping and chat functionalities, allowing us to better understand user behavior and improve website usability.