Best UK walking holiday for a group

7th June 2024

Although we are based in Northumberland, we offer our walking holidays in many other locations including The Cleveland Way, Cumbria Way, The Dales Way, Herriot Way, Isle of Man and The Pennine Way. We also offer some of our holidays as a taste of two trails where you get to experience the highlights of two holidays combined.

If you are thinking of planning a UK Walking Holiday with family, friends, colleagues, or an organization then there are a variety of things to consider. Here at Shepherds Walks Holidays, we are here to guide you and support you through the planning process and we will be with you every step of the way. We have put together this helpful guide to help you to think about your requirements and add some suggestions for you, this will help you in deciding which of our trails will suit your group. Once you have made a decision; we will ensure that everything is in place for us to provide you with the best holiday experience you could wish for.

The planning stages -

You will first need to discuss with your fellow walkers which trail is suitable for you all, discuss the distance you wish to all do each day and look at the trails that we offer. Each of our trails has the mileage calculated for each day’s walking. As well as the distance you will need to discuss the difficulty of the walking trail that you all wish to choose for your UK walking holiday. Our trails are all graded due to the difficulty.

Grade 1 – Easy

Grade 2 – Moderate

Grade 3 – Difficult

For example,

Hadrian's Wall 5-day - This holiday is graded as difficult as it has some fairly demanding days with the two middle days being 24 and 27 miles. Please only consider doing this walk if your group are fit enough to walk 84 miles in 4 days!

Northumberland Coastal Path Highlights - This holiday is graded as easy and is and is generally level with very few steep climbs and is clearly signposted from roads and way-marked throughout. Most stiles have been replaced with gates and the walking surfaces are generally good. The Northumberland coast is known for its sandy beaches, rolling dunes, and picturesque harbour villages, and this holiday gives you plenty of time to amble along the coast and enjoy the scenery.

Your group size -

Decide on the size of your group, we would recommend a group size of 6-8 people. (However, we are able to accommodate larger groups, just contact us with your requirements) A group of this size is easier for us to coordinate your transfers during your holiday and will also keep your costings down. It would also be useful to have a conversation with your group members in relation to your arrival and departure for both the start and finish of your holiday.

Will you all arrive together?

How will you arrive, will you arrive by car, train or plane?

This will determine if you require transfers from an arrival point to your first accommodation and a transfer to a train station, airport or car parking when your holiday finishes, again this will reflect in the costings.


Your room requirements -

Once you have decided on how many people will be in your group you need to think about your needs for the accommodation that we will book for you.

How many rooms will you require?

What type of rooms would you prefer? Single, double, or twin?

Will you require any extra nights, either at the beginning or end of your holiday?

The accommodation we use are Inns, family-run hotels, and Bed and Breakfasts. We endeavour to provide en-suite accommodation. The further in advance you book your holiday, the more chance we have of securing the best accommodation on your chosen trail. Often, we will have block booked the best accommodation the previous year. We want our customers to stay in the best possible accommodation. As we know the proprietors personally and we liaise with them regularly and they will go that extra mile to help us to help you whilst out on your route.

Bath House - Northumberland Coast Path

Which UK Walking Holiday would we recommend for a group?

As we have a lot of experience in booking UK Walking Holidays for groups, we would recommend The Dales Way as a fantastic holiday to walk with a group. Not just because of the amazing scenery and fabulous surroundings, but all of the accommodations are on the route, this means no transfers during your walking days, this will keep your costs down.


The Dales Way

The majority of this Grade 2 walk passes through the Yorkshire Dales National Park, over moors, across limestone pavements, through valleys, and alongside rivers. It gives a unique taste of this famous park to the walker.

The walk leaves the Yorkshire Dales for the finale as it crosses into Cumbria, fringing the Howgill Fells before culminating in the Lake District National Park on the banks of Lake Windermere.

This long-distance walk is particularly memorable, and the total length is 80 miles is the perfect introduction for newcomers to long-distance walking.

We have various options available for this holiday.

5 Days Dales Way Highlights

7 Days Dales Way

8 Days Dales Way


Which holiday will you choose?

Take some time to browse our holidays – please let us know if you have any questions, we are here to provide you with as much information that you may require to ensure that you choose the best holiday for your group. Please feel free to contact us.

It is important that as a group you all discuss and agree on which of our Shepherds Walks Holidays you all choose and are happy to walk together. On our website, you can click on any of the holidays available and choose to download a holiday dossier which will give you lots of information on our trails. There are also some useful FAQs to look at which will answer any queries you may have.


Bespoke Bookings

If there is a holiday that you would like to book but would like some changes made then please let us know and we can arrange a bespoke booking for your group. For example – You may wish to customise an existing trip to make it more difficult or easier, longer or shorter. You may wish to include some rest days so you can take in the surroundings and do some further exploring in our wonderful locations.

High Cup Nick - Pennine Way

Next Steps - What we do

Once you have placed your group booking, we will then begin to build your holiday for you. We will ensure we book the best accommodation available to your group and put all of your transfers in place along with all the luggage transfers. We will also ensure that we maintain contact with you and will notify you of anything you need to know in our planning process.

As we don’t cut corners, and provide the best customer care and service, we want to see you again and want you to speak highly of Shepherds Walks Holidays. This is why we are literally willing to go that extra mile. The information you receive at every stage will be clear and leave you asking no questions and looking forward to your holiday, knowing that you are in safe hands.


Why choose us?

We pride ourselves on our relationships with our customers, many who have walked numerous trials with us and are members of the Shepherds Walks Family.


Don’t just take our word for it -

Shepherds Walks were amazing from start to finish as was Hadrian's Wall! After a general search on Google for a company to use we settled with SW. Everything that was agreed on, itinerary, transfers, accommodation was spot on, thank you. Even the part, which was not in the itinerary, of taking forgotten engagement ring, wedding ring and eternity ring from one accommodation to the next by taxi to the very embarrassed wife was taken care of by SW without fuss or bother, thank you! The accommodation was brill as was the food and drink. We had the most amazing 6 days adventure.

 22nd Oct 2023 - Mark, Emma and Rufus the Border Terrier


Hadrian's Wall – Carlisle Arrival – Self Guided – 8 days

Thursday 22nd June 2023 Mike Hill

Shepherds Walks Holidays provided an excellent service in arranging the Hadrian's Wall Path walk.

The overnight accommodation was of a high standard with good facilities and excellent meals.

The baggage transfer went without a hitch and all prearranged taxis arrived promptly on time.

The courtesy and very prompt response to any questions raised with the Shepherds Walks Holidays team was much appreciated.

Overall, Shepherds Walks Holidays is to be highly recommended.


Shepherds Walks Holidays is an established local business providing guided, self-guided and bespoke walking holidays. So, what makes us so special? All our holidays have been created from a Shepherd's perspective, looking and appreciating the landscapes that we live and breathe and we embrace local cultures and traditions.

What are you waiting for?

Contact us

And let us provide you with the

Best UK Walking Holiday


Shepherds Walks Holidays


Our UK Walking Holidays 2024 

Hadrian’s Wall trail

St Oswald’s Way

St Cuthbert’s Way

Northumberland Coastal Path

Yorkshire Dales – 3 Peaks

Berwickshire Coastal Path

The Dales Way

The Cumbria Way

The Isle of Man

A Taste of 2 Trails

The Cleveland Way

The Herriot Way

The Pennine Way

Northern Saints Trail


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