Pennine Way - Walking and Cycling Holidays in the United Kingdom Pennine Way - Walking and Cycling Holidays in the United Kingdom Pennine Way - Walking and Cycling Holidays in the United Kingdom Pennine Way - Walking and Cycling Holidays in the United Kingdom

COVID-19 Update  | The ongoing safety of you as our travellers is our top priority. You've come to the right place as our style of travel is naturally adhering to social distancing guidelines. When booking your active UK or European holiday with Sherpa Expeditions, you can be assured with relaxed booking conditions - contact us to learn more. While at the same time we deliver after hours support and operational modifications to meet social distancing & safety guidelines during your travels in the UK & Europe. Learn more about our new health guidelines now.


The Pennine Way, a mountain journey across the backbone of England, became the very first British National Trail on April 24th 1965. It is a long, 268 mile (429 km) hike from Edale in Derbyshire to Kirk Yetholm in the Scottish Borders. It crosses some of the finest upland landscapes in England, from the Peak District, through the Yorkshire Dales, across the North Pennines and over Hadrian’s Wall in Northumberland, through the Cheviots and down into Scotland. It is iconic because it was the product of the post First World War mass trespass movement of often working class walkers with a socialist outlook. The walk was conceived by Tom Stephenson, secretary of the Ramblers Association, back in 1935. He could see it in the context of young people as a means of “opening  their minds to the beauty, the peace and the soul-satisfying gifts of high and lonely places,”  but it took until July 1951 before it was approved and a further 15 years before it could be officially opened due to legal wrangles, especially in Northumberland and in Edale, Derbyshire. Landowners were still keen to keep people off their land.

It has been said that the Pennine Way would have been up and running 30 years before it officially opened, had Tom and his cohorts accepted the original proposals that the route follow sections of metalled road over some areas. It is a reflection of his great tenacity that the final route has no long road sections at all. Some of the facets of the walk which did not appeal to walkers, such as the bleak bogs, have been improved by the judicious use of flagstone trails in some areas. This is not to say that that there will be no bogs to negotiate, especially after a spell of bad weather.  

Tradition has it that you leave from the Nags Head pub in the small Derbyshire village of Edale. The first day is quite a tester with long ascents over Kinder Scout, Mill Hill and Bleaklow Head. They say you will know by the end of the first day whether, barring injury, you will be able to complete the walk! There are some subtly beautiful attractions along the way, including the Derbyshire grit stone edges, the limestone scenery at Malham, the high Yorkshire peaks Pen-y-ghent, Cam High Fell, Great Shunner Fell then, highest of all, Cross Fell. There are many lesser hills that undulate until you pass over the Cheviot hills into Scotland. Other major attractions include the various waterfalls you will come across on the River Tees (and elsewhere), walking along the Roman Wall and visiting some special towns and villages such as Edale, Hebden Bridge, Malham, Thwaite, Keld, Middleton-in-Teesdale and Bellingham. There are a lot of farms, gates and stiles too, not to mention Roman forts dotted about.

Finally, you stroll into Kirk Yetholm, where tradition also has it that you go to the Borders Hotel and claim half a pint of beer and a completion certificate. The beer was originally funded by Alfred Wainwright, then his estate and currently by the Hadrian Border Brewery.  

Much of the walk is within the realms of 3 National Parks: Derbyshire, Yorkshire Dales and Northumberland. When it is not in these areas it is often darting across other very scenic areas, including the North Pennines Area of Outstanding Natural Beauty.      

It is reckoned that only about 2,000 people a year do the Pennine Way walk. This may compare with 25,000 or more on the Coast to Coast! The result is that although at some 'honey pot' areas such as Edale, Malham and Horton In Ribblesdale you will find dozens of day or weekend walkers, there will be long, lonely stretches where you will be alone and need to be able to navigate in all weathers.

The Pennine Way is nearly always to be found on serious walkers' bucket lists. For many, often it is the case of getting enough time off work to complete it in one go. However, the walk can be split into two halves, or even smaller sections if required. We offer the Southern and Northern sections as well as the full route.

Originally considered as a backpacking route, it was thought that most people would camp, and then until the late 1980s you could do nearly the whole route using youth hostels. Today a lot of hostels and quite a number of B&Bs and pubs along the way have gone. One thing walkers on this route cannot be is too fussy about their accommodation. To make a complete a booking without expensive taxi transfers, it will be necessary  to stay in a whole range of places.



We recommend undertaking the Pennine Way walk when it is late spring to early autumn in the UK (May – late September). In recent years rainfall has been fairly low in May and June, although we are talking about a vast area and the uplift created by the Pennines is notorious for creating cloud and rain. The climate of upland northern England is variable, with rainfall occurring throughout the year (though more likely from October to April). The sunniest month is generally July and average temperatures between April and October range from 4°C (39°F) to 19°C (67°F), although it will be cooler on the higher sections of the trail. In fact conditions high up, such as at Cross Fell, can feel 'arctic' even in summer months if you have a run of bad weather, but in good weather you may be able to sunbathe! You can occasionally experience really warm summer days when the temperatures approach the 30s. The other reason why May and June are generally good months is that spring flowers are out on some path sections, and you have very long day light hours in which the walk can be completed. 


The Pennine way is one of the most iconic long-distance walks in England and is graded 'Challenging'. In reality it is very similar in difficulty to the Coast to Coast walk, with days of similar length. However, what makes The Pennine Way more difficult is the longer time spent on the walk in general and the lonelier walking experience in particular.    
Sherpa Expeditions offers self-guided versions of the Pennine Way walk, so you can choose dates that best suit your interests. The walk can depart any day from 1 April to 25 September, subject to availability. 


The Pennine Way walk starts in Edale and finishes in Kirk Yetholm. To get to Edale by train you will first need to get a train to Sheffield or Manchester and then a trans-Pennine train to Edale (around 3 hours from London - the Sheffield route is quicker than the Manchester one) and then there is a short walk from the station to the accommodation, although they may be able to collect you if you give them advance notice. 

On finishing the journey you will need to take a bus or taxi to Kelso to link with other bus services to Edinburgh (trains, airport etc.) or to Berwick-upon-Tweed, from where you can join the National Rail network. We would probably recommend pre-booking a taxi to take you to Berwick-upon-Tweed, whether you are heading north or south. Visit Trainline if you would like to look at the journey involved.   


Our Walking Holidays on the Pennine Way