Cleveland Way Frequently Asked Questions

Planning a trip on the Cleveland Way can be daunting, especially if this is your first long distance walking holiday. We are often asked the following questions and I hope that you will find the answers useful.

Please don’t hesitate to contact us if you have any further questions.

A great source of information on the Cleveland Way is on the National Trail Website.  From here you can download your free walkers passport which will qualify you for a completion certificate of the trail aswell as offer you up to date news.

How fit do I need to be?

We offer a range of itineraries so you can choose your preferred daily distance so hopefully you will find an itinerary that suits your preferred level of activity. If you currently don’t enjoy an active lifestyle we suggest regular walking in hilly terrain supplemented by cardio vascular exercise for at least 6 months prior to your walk. A good gym or personal trainer will be able to draw up a personalised training programme.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as the Cleveland Way is extremely popular especially over April/May and July/August. You will find up to date availability on our website and we will always try and accommodate your plans.

What personal equipment do I need?

You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc. You can download a full equipment list from the downloads page of our website.

When is the best time of year?

Traditionally April/May has always been the most popular time of year because the theory goes that the weather is better. Although I believe any time between late March and October offers a wonderful experience.

Which direction should I walk?

We only offer this holiday from Helmsley to Filey in one clockwise direction as the baggage handlers only operate in one way.

Am I able to take my dog?

Unfortunately we are unable to accommodate walkers with dogs as many of the accommodation providers we use do not accept pets.

What happens if I can’t walk a stage?

You can use public transport or local taxis to continue to your next overnight stop.  The Moors Bus operates throughout the North York Moors.

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