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Holidays

Self Guided Walking: The Cleveland Way

England
Walk & Trek
Self-Guided
MODERATE MODERATE

Traverse the entire North York Moors National Park through classic moorland scenery and along dramatic coastlines on this self-guided walking holiday

Trip Code: MCL8
Holiday Grades
          

Our Holiday Grades Explained

To show the relative difficulty of our holidays, each trip is graded on a scale of 1 to 12, with 12 being the most challenging. Although we have tried to make our grading system as clear as possible, it cannot take into account your personal interests, abilities or experience. If you have any questions about the nature of a particular trip or its suitability for you, please read the 'Is this holiday for you?' section or contact us.

 1 - 3 LEISURELY
1 - 3 LEISURELY

Suitable for most people in good health, holidays at this grade include only limited amounts of activity.

View leisurely holidays
4 - 6 MODERATE
4 - 6 MODERATE

Suitable for reasonably fit individuals, such as weekend walkers and cyclists. There can be the occasional more difficult day.

View moderate holidays
7 - 9 CHALLENGING
7 - 9 CHALLENGING

Physically challenging holidays, where you need to be prepared before you go.

View challenging holidays
10 - 12 TOUGH
10 - 12 TOUGH

Our toughest holidays, involving many long days, often in isolated areas. A high level of fitness and previous wilderness and mountain experience is essential.

View Tough holidays

Self Guided Walking: The Cleveland Way

Highlights
  • Considered a classic trail for its variety of landscapes and seascapes over its 100 mile course through the North York Mors National Park
  • From Helmsley to Whitby, expect characterful towns with a wealth of heritage and charming villages dotted along the coast
  • Enjoy brilliant panoramas of purple heather and dramatic clifftop walking along the wild North Sea
  • Dog-friendly itinerary is available and we can organise the daily transfer of your dog’s food, bed and towels
  • Extensive route notes, recommendations for local meals, daily luggage transfers and B&B in local guesthouses included in the holiday price

At a Glance
  • Self-guided
  • 7 days walking
  • Average of 21 km per day walking
  • Dog-friendly accommodation options
  • Packed lunches available on request
  • Recommendations for excellent local meals
  • Join In Helmsley / Ends in Filey

Accommodation & Meals
  • 8 Breakfasts
  • 8 nights Guesthouse
Overview

A trail know for the diversity of its scenery, the Cleveland Way follows a horseshoe direction around the beautiful North York Moors National Park. Running for over 100 miles from the historic market town of Helmsley, the trail first explores the park’s open moorland, splendid with purple heather, until it reaches the awe-inspiring coast where you’ll walk above some of England’s highest sea cliff.

The trail is considered a classic not just because of the rich and varied landscape it passes but also because of the wealth of heritage you can enjoy along the way including Rievaulx Abbey, the White Horse of Kilburn, Gisborough Priory, Whitby Abby and Scarborough Castle. The trip includes all accommodation, breakfast and full luggage support meaning you can travel light and concentrate on the lovely scenery and historic sites.  

This is just one of 8 self-guided walking itineraries we offer including the entire 106 mile route – you can choose to take the entire route more easily over 11 days walking, or split it into two sections or just walk the highlights. Please ask for details. 

We also have a dog-friendly itinerary for this trip and can arrange to have your dog’s food, bed and towels transferred daily too.

Is this holiday for you?

The route covers rolling countryside and moorlands, but not mountains. If you are a regular walker this route should be within your capability.

Terrain: A walk of two halves – the North York Moors are rolling, sometimes remote, and up to 300m/1000ft high . The coastal path follows the cliffs with frequent descents to coves and beaches.

What’s it like underfoot? On the who …

The route covers rolling countryside and moorlands, but not mountains. If you are a regular walker this route should be within your capability.

Terrain: A walk of two halves – the North York Moors are rolling, sometimes remote, and up to 300m/1000ft high . The coastal path follows the cliffs with frequent descents to coves and beaches.

What’s it like underfoot? On the whole the paths are well defined and maintained, but at times it can be rough underfoot with some muddy paths, so good footwear is essential.

How much up & down? There are climbs of up to 300m some of which can be quite steep, through the Moors section, and short, sometimes steep climbs from sea level along the coast.

Signposting: Generally good.

Navigation: Pretty straightforward, but you may encounter hill fog or low cloud on the North York Moors, so make sure you can navigate.

Why KE?

We operate this trip in collaboration with our sister company Mickledore Travel, which is also based in Keswick in the Lake District. Mickledore have a long tradition of operating self-guided walking holidays along some of the finest trails in England, Scotland and Wales. Route notes, maps, luggage transfers and bed & breakfast accommodation in the best B&Bs, guesthouses and inns along the way are all included.

Recommendations are also made for the best places to find delicious local meals at each night stop.

Mickledore have a near perfect customer satisfaction score (99%), and we have no doubt that you will find their knowledgeable and friendly team able to answer even the most detailed of questions.

Different durations of this holiday are available on request, as is dog-friendly accommodation for those wishing to bring their four-legged friends along for the walk.

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