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Self Guided Walking: The Cleveland Way

England
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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.

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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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Itinerary

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Arrive at your accommodation in Helmsley

Accommodation

Guesthouse
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The first section of the Cleveland Way provides an easy woodland walk across the beautiful landscape of the Rye Valley, passing the ruins of Helmsley Castle and later the medieval Rievaulx Abbey. The walk then rises gently to the flat limestone plateaux of the Tabular Hills. It is also worth allowing time to visit the Kilburn White Horse, just before Sutton Bank. From Sutton Bank the walk is relatively flat, following the western edge of the Hambleton Hills overlooking the Vale of York. After Black Hambleton you drop down to the idyllic setting of Oakdale's reservoirs, en route to Osmotherley.

Accommodation

Guesthouse

Meals

B

Ascent

1002 M

Distance

34 KM
Hide Details

This is the most strenuous section of the trail, as the route follows the northern escarpment of the moors, broken by a series of valley's cutting into the uplands between Huthwaite Green and Clay Bank Top. After Clay Bank Top a steep climb leads up to Round Hill, the highest point on the route, where tremendous views can be enjoyed. The route then descends gradually to Kildale which is studded with signs of the past - waymarkers, boundary stones and burial mounds.

Accommodation

Guesthouse

Meals

B

Ascent

843 M

Distance

18 KM
Hide Details

Today's walk is dominated by an ascent of Easby Moor, to Captain Cook's Monument, and then the moorland 'Matterhorn', Roseberry Topping. Although only 300m (1000ft) high, this distinctive conical hill is prominent in the landscape. From the top the views are excellent.

Accommodation

Guesthouse

Meals

B

Ascent

890 M

Distance

32 KM
Hide Details

Farmland, woodland and a riverside path lead onto the coast at Saltburn-by-the-Sea. From Saltburn the route heads up Hunt Cliff and along a section of dramatic cliffs to the highest point on the east of England at Rock Cliff. This route takes you down to sea level on three occasions and through the pretty villages of Staithes as you make your way to Runswick Bay.

Accommodation

Guesthouse

Meals

B

Ascent

898 M

Distance

26 KM
Hide Details

Dramatic coast paths lead onto Whitby, with its fine harbour, fossil filled cliffs and old town connections with Bram Stoker's Dracula! A visit must be made to the imposing remains of Whitby Abbey high above the town. Whitby and Robin Hood's Bay are separated by an easy cliff top walk.

Accommodation

Guesthouse

Meals

B

Ascent

717 M

Distance

23 KM
Hide Details

Between Robin Hood's Bay and Scarborough the route encompasses ever-changing scenery, with the Flyingdales Moor to the west and the North Sea to the east. There are three steep descents and ascents along this path, where the sea interrupts the cliff top walk. The arrival into the seaside town of Scarborough will provide you with another type of scenery, with its grand beaches, swish hotels and traditional seaside entertainment!

Accommodation

Guesthouse

Meals

B

Ascent

666 M

Distance

23 KM
Hide Details

On leaving Scarborough, notice the vibrant colours from the South Cliff as you make your way to the final cliff top trail. The view of continuous coastal cliffs continues from Cayton Bay until your final destination, Filey.

Accommodation

Guesthouse

Meals

B

Ascent

414 M

Distance

18 KM
Hide Details

Enjoy a relaxing breakfast at your accommodation. Depart after breakfast.

Meals

B
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The Route
Point Point
Direction Direction
Trek

Essential Information

We've compiled some of our Frequently Asked Questions to help you learn more about this amazing trip.

  • All accommodation as described
  • Meals as described in the Meal Plan
  • Self-guided information pack containing your map and route notes
  • Luggage Transport

  • Travel Insurance
  • Evening meals
  • Packed lunches (can be booked at an additional cost)
  • Off road parking (available at most locations on request)
  • Transport to the start and away from the finish
  • Personal equipment
  • Any additional activities/excursions indicated as optional

This holiday is operated by our sister company, Mickledore Travel. KE is not acting as an agent, but is marketing the holiday on Mickledore’s behalf. All bookings and payments will be processed by Mickledore, and you will enter into an agreement directly with them under the terms of their booking conditions.

You will be posted your self-guided holiday pack once we have received the balance (normally around 8 weeks before the start of your holiday).  We supply one holiday pack per booking and this will be posted to the person that made the booking. Extra packs can be purchased at £30 per pack. Please contact us a minimum of 6 weeks in advance if you require an extra pack. 

Your holiday pack comprises of:

  • Your itinerary with details of each night’s accommodation; information on your evening meals, as well as luggage transport and transfers, (where applicable).
  • Directions and detailed maps to each accommodation
  • A guidebook that describes the route in detail, and covers the whole route with a series of maps, as well as providing a wealth of background information.
  • Map(s) which cover the entire route(s).
  • Luggage Tags (if luggage transport booked) which the luggage courier will use to identify your bags.
  • Information on local facilities, such as cafes and other recommended places to eat, cash points, taxi companies, etc.

As part of the standard charge we will issue the following:

  • 1 guidebook and map for up to 4 people
  • 2 guidebooks and maps for 5-7 people
  • 3 guidebooks and maps for 8 people or more

You may purchase extra copies from us at a discounted price.

This holidays starts at your accommodation in Helmsley. All of our self-guided holidays are sold on a land only basis allowing you the flexibility to choose the travel method which best suits you.

Detailed instructions on getting to your first night's and returning from your last night's accommodation by car, or on foot from the nearest train or bus station, will also be included in the holiday pack on individual accommodation maps.

This holiday is on a B&B basis. Packed lunches are available on request, and we have many recommendations for excellent local meals.

Water from the taps is perfectly drinkable on this holiday - please use this to fill your personal bottles for your daily activities. We do not encourage the purchase of single-use plastic bottles.

Your evening meal isn’t included in the package, but we include full details and recommendations for each evening meal in your itinerary. You will normally be within walking distance of a pub and/or restaurant, or where there is good food available at the accommodation, we’ll book that for you. Allow about £20 per person per night. Your evening meal isn’t included in the package, but we include full details and recommendations for each evening meal in your itinerary. You will normally be within walking distance of a pub and/or restaurant, or where there is good food available at the accommodation, we’ll book that for you. Allow about £20 per person per night. 

Pack lunches can be provided on this holiday for an additional cost, from £55 per person. We recommend this as there will not always be a handy shop or cafe on the route.

One of the great features of our Cleveland Way holidays is the quality of the accommodation, including small country house hotels, guest houses, bed and breakfasts and farm house accommodation. In selecting the accommodation we look for helpful, friendly hosts with good quality, characterful accommodation close to the trail. We always try to arrange en suite accommodation, i.e. rooms with their own bathrooms for each night of your stay. However, in some of the more remote locations accommodation is limited and occasionally we may have to book rooms with shared bathrooms for one or two nights of your holiday, (especially if the booking is made at short notice), but we will always let you know if this is likely to be the case.

Single Rooms We are happy to book single rooms on this walk but cannot normally book more than 2 for any one group. Single room bookings include a supplement.

For each holiday there is a minimum number of participants required to enable it to go ahead. Once the minimum number is reached, the trip status will change from 'Available' to 'Guaranteed to run'. You can check the trip status for each departure in the ‘Dates and Prices’ table. Other than in exceptional circumstances, we will not cancel a trip once it has achieved this guaranteed to run status so you are free to proceed with your international flight booking and other travel arrangements.

The information that we provide is for UK passport holders. A passport with 6 months remaining validity at the end of your stay is generally required, and you should have at least 2 blank pages for each country that you visit.

It is your responsibility to ensure that you have the correct travel documents and visas for your holiday. Please ensure that you check for the latest advice before travel. For the most up to date information on entry requirements, please visit the UK Government website.

If you have a severe allergy please inform the KE office before you travel. We will do all we can to help, but we cannot guarantee an allergy free environment on KE trips. You will need to carry your own treatment for the allergy with you, as 'adrenaline auto-injectors' are not carried as standard by KE leaders and staff. You should inform your leader on arrival of your allergy, and let them know where you keep your adrenaline pen.

Severe Allergies

Please inform our KE Sales and support team of any severe allergies you may have before travel. We will always do our best to help but we are unable to guarantee an allergy free environment on our KE trips. We advise that you always carry your own treatment for the allergy with you such as 'adrenaline auto-injectors' if required.  We also recommend that you discuss this with your accommodation on arrival so that they can better assist you.

The unit of currency in the UK is Sterling.

As a reputable tour operator, KE supports the British Foreign, Commonwealth and Development Office's ‘Travel Aware’ campaign to enable British citizens to prepare for their journeys overseas. The 'Travel Aware' website provides a single, authoritative source of advice for all kinds of travellers and we recommend that before travel, all KE clients visit the official UK Government website at travelaware.campaign.gov.uk and read the FCDO Travel Advice for their chosen destination. North Americans can also check out the U.S. Department of State website: www.travel.state.gov for essential travel advice and tips.

KE treat the safety and security of all clients as the most important aspect of any trip we organise. We would not run any trip that we did not consider reasonably safe.  Should the FCDO advise against travel for any reason, we will contact everyone booked to travel to discuss the situation.  We receive regular updates directly from the FCDO and are in constant touch with our contacts on the ground.  If you have any questions about government travel advice, please call our office.

KE do not encourage the use of single use plastic items. We are ensuring that our agents all over the world are working together to reduce the problem and educate those around them. We are leading by example in our KE office by reducing our plastic use.

It is an essential condition of joining a holiday with KE Adventure Travel that you have a valid travel insurance policy to cover the cost of medical treatment and to protect the value of your holiday in the event of cancellation.  When taking out insurance please ensure the policy you choose covers you for the activities and altitude included in your itinerary.

For appropriate insurance cover we recommend Campbell Irvine Direct.  Please go to our Travel Insurance page for further information and to get a quote.

Where luggage transport is included in the price, this will be a standard of 1 piece of luggage per person, usually up to 20kg in weight. On some routes the weight limit may be less, but we will advise you if this is the case. If you leave your luggage at your accommodation in the morning, it will be waiting for you on arrival at the B&B that evening. Any extra bags can be transported (at an additional charge) as long as they are pre-booked.

On certain holidays we also offer a storage service for extra luggage not needing to be transported for the holiday. Please contact us for for information on which holidays and a quotation.

All you need to carry is a small day sack to hold your waterproofs, personal items, packed lunch, map, guidebook and camera. You should be prepared for all weathers, at all times of year.

YOU SHOULD BRING THE FOLLOWING ITEMS:

  • Walking boots – need to be comfortable and well broken in
  • Several pairs of thick walking socks
  • Mittens/gloves
  • Warm hat and/or sun hat
  • Raincoat: (waterproof and windproof with a hood)
  • Waterproof trousers
  • Thermal long-johns & thermal top
  • Jacket
  • Fleece tops
  • Fleece or polypropylene trousers (no denim or cotton)
  • Spare clothing for the evening
  • Shorts and t-shirt (ideally made from synthetic fibres)
  • Map case
  • Compass
  • Torch: with spare batteries
  • First aid kit: insect repellent, sunscreen, blister kits, pain relief and assorted bandages
  • Water bottle
  • Walking poles (if you already use these)
  • Small day sack (20-30L) for carrying your personal items
  • Day sack liner / black bin bag / day sack waterproof cover
  • Camera and memory card
  • Phone and charger
  • Binoculars
  • Sunglasses
  • Whistle
  • GPS (if you already use one)

Many of the equipment items listed above are available from Cotswold Outdoor - our 'Official Recommended Outdoor Retailer'. When you book a holiday with KE you will receive a 12.5% discount with Cotswold Outdoor, Snow+Rock and Runners Need. The discount code can be downloaded from your MyKE account and you can use this code at the checkout, either in store or online.

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