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Call us on 01707 331133

  • Mon to Fri09:00 - 17:00
  • Saturday09:00 - 13:00
  • SundayClosed

The Cleveland Way National Trail

Some of the most varied and impressive scenery on a long-distance path in England

  • Yorkshire

  • 10 nights
  • Half Board
  • Continuous Route Walking Holidays

  • Jun




What does this mean?

Tour codes: 78350

Book now from £1,359

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Our holiday walking grades


Grade 6

Full day walks with appreciable amounts of ascent and descent.

These walks are in more remote areas such as Andorra or northern Portugal.

Similar to Grade 5, but with most of the walks at the upper level of ascent/descent, time and distance.


Holiday Highlights

  • Dramatic clifftop walking with views over the North Sea
  • Robin Hood's Bay with its cliff-hanging cottages
  • A walk of contrasts through glorious North Yorkshire - wild moorlands, superb coastal views & dramatic cliff tops
  • The remains of the Rievaulx Abbey and the gothic 13th century Whitby Abbey

Starting in Helmsley, a lovely market town on the southern side of the North York Moors, we walk in a clockwise direction through some of the most varied and inspiring scenery in England. Highlights include, Sutton Bank, and its White Horse carved in the hillside, Roseberry Topping, as distinctive a hill as you will find, Whitby with its ruined hilltop abbey, Staithes a most picturesque harbour village, Scarborough and finally Filey, the well-known seaside town. 

The path can be split into two sections. The first half is inland heading north passed through the Cleveland Hills to reach the sea at Saltburn. From here the path follows the coast south through Staithes, surely the most picturesque village on the route to Whitby, Scarborough and Filey. The scenery on inland and coastal sections is wildly different but everyday and indeed every hour another wonder will unfurl on your way. 

We split the 109-mile path into 9 day walks and our holiday offers the entire route. Some days are easier and some more challenging. We stay in two hotels as close to the path as possible, with transport provided out and back to the trailheads, as necessary. This means you don’t have to pack up each night or carry anything more than a day sack. Our hotels have been carefully chosen to offer comfortable accommodation and minimise the amount of travelling required.

  • Half board en suite accommodation in two centres
  • Private coach transport to and from the trailheads each walk day
  • Private bus transfer to pick up your car at the end of the holiday, if required
  • Services of a dedicated tour leader
  • Entrance fees (unless otherwise specified)
  • Personal expenses (such as your bar bill)
  • Lunches
  • Discretionary tips
  • Optional excursions
  • Travel Insurance

Holiday Information

Click the button below for a detailed Holiday Information Sheet containing all the particulars about this trip.

NOTE: Itineraries and Holiday Information Sheets can vary by a specific date chosen

View Holiday Information Sheet

Itinerary & Travel

Itinerary Details

Whilst every effort will be made to adhere to the outlined itinerary and advertised programme, local conditions can change due to weather or other unforeseen circumstances. This may mean that routes and timings need to be amended or the order of days may change, sometimes at short notice.

Due to the ongoing COVID-19 pandemic, we may unfortunately need to withdraw a tour that is currently confirmed to operate and we therefore reserve the right to cancel your booking. We would always do our utmost to give you plenty of notice should we have to do this. Selected elements of this tour, including local attractions and restaurants, may change at late notice. Please ensure you have valid insurance cover before you travel.

Your Itinerary

Day 1

Arrival day - Great Broughton




Independent travel to The Wainstones Hotel in Great Broughton. Check in is from 2pm. Meet your tour leader at approximately 6pm in the hotel for a briefing before dinner. Dinner each evening is in the hotel restaurant.

Day 2

Hemsley to Sutton Bank


Breakfast & Dinner


  • Time

    6 hours

  • Distance

    12 miles

  • Ascent/Descent


This is an outstanding day to start our walking programme. We take transport to Hemsley at the south of the North York moors. Helmsley is a delightful market town. Helmsley Castle is clearly visible as you start to climb out of the town. 

Our trail heads west passing close by the impressive ruins of Rievaulx Abbey and on to the white horse at Sutton Bank. From here there are spectacular views west across to the Yorkshire Dales.

Day 3

Sutton Bank to Osmotherley


Breakfast & Dinner


  • Time

    6 hours

  • Distance

    12 miles

  • Ascent/Descent


From Sutton Bank we turn north and walk towards Osmotherley with views out west accompanying us during the day. Osmotherley is famed as the start as Lyke Wake Walk, the 40-mile coffin route across the water shed of the moors. We meet the path again at Ravenscar in 5 days’ time.

Day 4

Osmotherley to Clay Bank


Breakfast & Dinner


  • Time

    6 hours

  • Distance

    12 miles

  • Ascent/Descent


From Osmotherley we continue along the escarpment above Mount Grace Priory and turn east to Clay Bank. Today we have views north across Teesside and the distinctive outline of Roseberry Topping.

Day 5

Clay Bank to Gribdale Gate


Breakfast & Dinner


  • Time

    6 hours

  • Distance

    13 miles

  • Ascent/Descent


We continue along the northern escarpment and through moorland scenery before descending to the pleasant village of Kildale. The railway that goes through the village is the Esk Valley line that goes out to Whitby.

Day 6

Gribdale Gate to Saltburn


Breakfast & Dinner


  • Time

    7 hours

  • Distance

    13 miles

  • Ascent/Descent


Today we get back into civilisation walking north to arrive at the attractive seaside town of Saltburn. On the way we make a detour to climb Roseberry Topping, one of the more distinctive landmarks in the country. On arrival at Saltburn some may like to take the opportunity to enjoy a paddle in the sea. We return to the Wainstones Hotel for our last night. Tomorrow our luggage is transferred to our hotel in Robin Hood's Bay.

Day 7

Saltburn to Runswick Bay


Breakfast & Dinner


  • Time

    6 hours

  • Distance

    13 miles

  • Ascent/Descent


We follow the coast for the rest of our walk. From Saltburn we head east and south. The highlight village today and probably the whole walk is Staithes. A classic old fishing village, it is a lovely place to enjoy a drink, before continuing on to Runswick Bay. We then transfer to our hotel in Robin Hood's Bay in time for dinner.

Day 8

Runswick Bay to Robin Hood's Bay


Breakfast & Dinner


  • Time

    7 hours

  • Distance

    15.5 miles

  • Ascent/Descent


This section covers some outstanding coastal scenery as well as visiting popular seaside resorts such as Whitby and Robin Hood's Bay. The ruined abbey above the town of Whitby will dominate the views for a good part of the day today. We walk into Robin Hood's Bay and to our hotel.

Day 9

Robin Hood's Bay to Scarborough


Breakfast & Dinner


  • Time

    7 hours

  • Distance

    16.5 miles

  • Ascent/Descent


This classic stretch of the trail heads up towards the distinctive heights of Ravenscar; the other end of the Lyke Wake Walk. 

Heading south from Ravenscar, the trail drops into the delightful wooded bay of Hayburn Wyke. This is a fantastic spot to stop by the waterfall and admire the stone pebble beach. On reaching Scarborough we can enjoy an exhilarating walk around its promenade from North Bay to South Bay. 

Day 10

Scarborough to Filey Brigg


Breakfast & Dinner


  • Time

    4 hours

  • Distance

    8 miles

  • Ascent/Descent


This final length has some stunning cliff and coastal scenery to appreciate as you walk to the lovely old Victorian resort of Filey. The walk passes above the beautiful expanse of Cayton Bay before you enjoy the last few miles through to the stunning geographical location of Filey Brigg, a birdwatcher's paradise. A fitting end to an inspiring walk. 

Our coach to Robin Hood's Bay will immediately continue to Great Broughton so that we can pick up our cars from the Wainstones Hotel (if required). The drive is approximately one hour each way. 

Day 11

Departure day



Departure from the hotel after breakfast. Check out is by 11am. We hope that you have enjoyed your holiday and look forward to welcoming you on another soon.  

From (GBP)£1,359

Departure dates for your selected tour

26th Jun 2022 - 6th Jul 2022 (10 Nights)

28th Aug 2022 - 7th Sep 2022 (10 Nights)

25th Sep 2022 - 5th Oct 2022 (10 Nights)

Travel Details

Private coach transport to and from the trailheads each walk day is included.

Nearest mainland railway stations:
Northallerton - start of the holiday (16 miles)
Scarborough - end of the holiday (15 miles)

Please note that if you are driving to Great Broughton to join our holiday, you will need to travel back to The Wainstones Hotel in Great Broughton at the end of your stay in Robin Hood's Bay (the end of the holiday) to collect your vehicle. This is not included in your holiday price. We can however offer you a complimentary transfer back to collect your vehicle on the penultimate day of your holiday. You can then drive to Robin Hood's Bay to collect your vehicle on your last night and arrive in time for dinner. 

Free car parking is available at The Wainstones Hotel and the Victoria Hotel. 

If you are planning to arrive in Great Broughton using public transport, we will provide a private coach transfer to Robin Hood's Bay on day 7. 


Accommodation information

Below is the accommodation featured on this holiday across all departure dates. Please refer to the Itinerary for more detail about each night's accommodation for each departure date.

The Wainstones Hotel, Great Broughton

Located conveniently to the Cleveland Way National Trail, this family run traditional hotel and pub together with separate restaurant is the perfect base for the first 6 nights of this holiday. 

The hotel has a small amount of comfortable en suite bedrooms, each with TV, complimentary Wi-Fi and tea and coffee making facilities. Breakfasts and dinners are taken in the hotel throughout your stay, where the hotel uses fresh local produce offering traditional meals. 

The hotel has a large car park and you will be required to leave your vehicle here for the duration of the holiday and return to the hotel to collect your vehicle at the end of the holiday. 

The remainder of the holiday (4 nights) will be based at the Victoria Hotel in Robin Hood's Bay. 

Victoria Hotel, Robin Hoods Bay

Boasting stunning cliff-top views over Robin Hood’s Bay, this grand, Victorian hotel is on the edge of the North York Moors. It offers homemade food, rooms with Egyptian cotton bedding, and a sea view tea room. Due to the nature and age of the building, there is no lift in the hotel and bedrooms may be split between floors. If you require help with your luggage, hotel staff will be more than happy to help you. 

Light and elegant, the rooms all provide a flat-screen TV, free Wi-Fi, and free tea and coffee for guests to relax with. Every bedroom has a private bathroom with free toiletries and a hairdryer.

The hotel has car parking, however spaces are limited. If required, there are pay and display car parks very close to the hotel. 

Trip Information

All the details you need

Holiday Grade

This is a Grade 6 holiday which includes full day walks with appreciable amounts of ascent and descent with walks in some remote areas. Paths are mostly good, but there may be some steep and rough ground. Walks will last up to 7 hours each day and could involve as much as 750m of ascent and descent. 

Please note that this is a holiday at the top of the grade and being a consecutive 9 walking day holiday, it is essential you are fit for the grade. It is also important to note that there are two days of the holiday where 16 miles each day are covered consecutively. 

See the 'Proposed Itinerary' section for more information. 

Walks & Excursions

The Cleveland Way National Trail is a 109 mile walking trail through beautiful and ever changing scenery. Officially opened in 1969, it was the second recognised National Trail in England and Wales. 

Starting from the attractive town of Helmsley, the route passes through heather moorland of the North York Moors National Park before reaching the coast at Saltburn-by-the-Sea, followed by walking along the coastline to Filey.  

Local Transport Costs

All local transport costs in conjunction with the advertised activity programme are included in the holiday cost. There may be occasions where additional visits or excursions are added to enrich your experience, these will be paid for locally by you if you choose to participate. Local transport can be a mix of private hire coaches, taxis, local buses and ferries depending on the itinerary.

Optional Excursions

A range of local excursions and activities may be available to book at your destination through a local operator. We have no involvement in such activities or excursions which are not run, supervised or controlled in any way by us. Your contract will be with the local activity supplier and we accept no responsibility for their actions or omissions.

Spending Money

Holiday Budgeting

When budgeting for your holiday, you will need to consider drinks, any meals not included in the holiday price, non-included entrance fees, optional excursions you may choose to participate in locally and any souvenirs or additional services such as laundry. A general guideline for lunches and drinks is £10-£20 per person per day.


Although entirely at your own discretion, tipping is an important aspect of tourism and hospitality life and expectations are fairly high. In order to simplify tipping, we strongly recommend that you allow your leader to take care of making sure tips are given to hotel and restaurant staff and to local guides and drivers. This will be done using some funds provided by us together with, if you wish, a contribution from you, which he/she will collect during the holiday.

Tour Leaders & Local Guides

Tour Leaders

Your tour leader makes the world of difference to your holiday and ours are as passionate about discovering the world on foot as you are. They're resourceful, organised and widely travelled. They will handle all the local administration and other needs that might arise to ensure that you don't have to worry about planning your days and you can enjoy your holiday. Although leading group holidays, they won't forget that every group is made up of individuals. Each tour leader has their own individual style, talents and professional backgrounds and all are trained, qualified, experienced and dedicated to making your holiday as enjoyable, interesting and inspiring as possible.

Leader's Evening Briefing

Each evening, your tour leader will discuss with you the programme for the following day. This will be your opportunity to discuss the details and ensure the planned activities suit your walking ability. If you have concerns on clothing or equipment, this can be discussed then also. If you do not wish to join the organised group programme, please let the leader know.

Your Travel Details

To reach Great Broughton…

By car: from the South – take the A1(M) to A168 in North Yorkshire. Follow the A168, A19 and A172. At the roundabout, take the 4th exit onto B1257. Turn left onto the High Street and the Wainstones Hotel will be on the left hand side. 

By car: from the North - follow the A66 from the direction of Carlisle or the A1 from the direction of Newcastle upon Tyne until you teach Northallerton or Middlesbrough. Get on the A19, take the A172 to Stokesley, then follow the B1257 to the High Street. The hotel will be on the left hand side. 

Please note that if you are driving to Great Broughton to join our holiday, you will need to travel back to The Wainstones Hotel in Great Broughton at the end of your stay in Robin Hood's Bay (the end of the holiday) to collect your vehicle. This is not included in your holiday price. We can however offer you a complimentary transfer back to collect your vehicle on the penultimate day of your holiday. You can then drive to Robin Hood's Bay to collect your vehicle on your last night and arrive in time for dinner.

Free car parking is available at The Wainstones Hotel and the Victoria Hotel. 

If you are planning to arrive in Great Broughton using public transport, we will provide a private coach transfer to Robin Hood's Bay on day 7. 

By rail and coach: the nearest bus and railway station is at Northallerton. Direct trains to Northallerton are available from various locations. A bus can be taken from the railway station (number 89) which will take you a short distance from the hotel front door. The journey may take up to 50 minutes by bus. Alternatively a taxi is an option and this may cost between £35 - £45. 

UK rail information:

UK coach information:

Route planning to and from Great Broughton and Robin Hood's Bay;

The AA and RAC both offer free and detailed on-line route planning facilities on their websites which may help you find our hotels. Details can be found at: and 

You may also wish to look at the following website for advice on the best way to travel to the hotel:

Personal Details Check

To ensure that we can accurately administer your holiday arrangements, please confirm that the personal details we hold for you are up to date and that you have provided the information we need to secure your holiday travel and accommodation arrangements. Please check your passport details, date of birth and any other important details necessary for us to properly manage your holiday booking. You can view and update information already provided, and add details not yet asked for, by using the Manage My Booking facility on our website, or by calling our Sales and Reservations team on +44 (0)1707 331133. When you receive your booking confirmation please check the details as soon as possible.

Entry Requirements

Passport Information for United Kingdom

Any non UK or EU citizens may be subject to passport, identity card or visa requirements to enter the United Kingdom.


Breakfasts and dinners are included in the holiday cost and will be taken at each hotel. Lunches are not included.

Packed lunches may be purchased from the hotels or supplies can be purchased locally. It will involve a drive to the nearest shop from the first centre, however there are plenty of shops within walking distance from your second centre, Robin Hood's Bay.  

Footwear & Kit List


Lightweight waterproof walking boots with a good moulded sole (such as Vibram or similar) and a deep tread and which provide ankle support are strongly recommended and may be essential for some walks. 

General Kit List

Outdoor activities are always safer and more enjoyable if you are prepared.

If you have not travelled with us before the following list might be of use:

  • Waterproof jacket (Goretex or similar) and trousers
  • Lightweight quick-drying trousers
  • Walking T-shirt/shirts
  • Walking socks
  • Fleece or jumper
  • Sun hat, sunglasses, lip salve and sun block
  • Warm hat and gloves (if appropriate)
  • Swimwear (if appropriate)
  • Day sack (this should be able to carry all you would need for the day's activity)
  • Day sack liner
  • Water bottle - at least 1 litre capacity (more than 1 bottle may be required)
  • Basic first aid kit
  • Lunchbox
  • Walking poles (should you find them useful)
  • Sit mat

This list is not exhaustive and every walker is different and may have their own preference.

Travel Documents Checklist

Documents and Information to take with you:

  • Holiday money
  • Credit or debit cards (and separate details of who to call if lost)
  • Car parking ticket and car park directions (if prebooked)
  • Coach or rail travel tickets (if prebooked)
  • Holiday booking confirmation document
  • Travel insurance details (if applicable)
  • Details of any medical condition or allergy your holiday leader should know about

Water To Go

An alternative to bottled water from single-use sealed water bottles is filtered water from a refillable bottle containing its own water filter such as a Water-to-go bottle available from Just fill up from any water source and save the environment from disposable plastic bottles.

We have negotiated an exclusive 15% discount with our partners Water-to-Go for you as a thank you for helping the environment. Please go to their website at and enter the code RWH17 when ordering. In addition, Water-to-Go will match the discount with a donation to our charity, Heart & Sole, which will allow us to continue to make a difference in the countries you visit on our holidays.

Maps, Guidebooks & Other Information

Maps, Guidebooks & More

Our intended route is covered by the following maps and guidebooks:

Ordnance Survey Explorer series (1:25,000):

Explorer 301 Scarborough, Bridlington & Flamborough Head
Explorer OL26 North York Moors Western area
Explorer OL27 North York Moors Eastern area

You might also like to read:

Cicerone, Walking the Cleveland Way and Yorkshire Wolds Way guide book or the Trailblazer guide to walking the Cleveland Way.

More information can also be found at

The Map Shop

If you cannot find the maps or books locally we recommend:

The Map Shop
5 High Street
Upton upon Severn, Worcs

Tel: 01684 593 146

If you key many of the local places mentioned in this holiday fact sheet into YouTube, you will find a vast array of spectacular footage of the area.


Visit the following websites for an idea of the climate in your destination:

Staying Healthy On Holiday

Health requirements can change at any time. It is your own responsibility to ensure that you inform yourself from a professionally qualified source on, and comply with, such requirements at least 6 to 8 weeks before departure. Advice on vaccinations is available from your GP.

Health Advice for United Kingdom

No compulsory immunisations are required for holidays in the UK although you should be up to date with the usual immunisations recommended for life in Britain. Tetanus immunisation is recommended.

Further Travel Advice

For further advice please visit:

You might wish to take a small bottle of antibacterial hand gel with you for times when you're unable to wash your hands.

Travel Insurance

Although not compulsory for British and EU citizens resident in the UK, we strongly recommend that you take out travel insurance to cover you in the event of eventualities such as unexpected cancellation, accident or illness before your holiday or the loss of personal possessions.

Visitors who are not British Citizens (or who are not EU citizens resident in the UK), must be adequately insured to join our holidays and will be unable to participate in our local walking and other activity programmes without being able to demonstrate that you have valid travel insurance.

Personal Safety

The UK Foreign, Commonwealth & Development Office provides up to date information on security and local laws for travellers, together with current passport and visa information, at Please take a few minutes to look at the current advice on your planned destination.

Please be aware of what's going on around you, take sensible precautions with your credit cards and passport and avoid displays of wealth such as wearing expensive jewellery or watches. Do not carry more cash on you than you will need for each day, and we recommend that a money belt is used.

Cultural Awareness

Responsible Travel

We're committed to ethical tourism in all our destinations. Our holidays are designed for you to discover the essence of the country you are visiting. Travelling in small groups not only gives you an up close and personal experience of your destination, but minimises your impact on the immediate environment. We feel that the most important starting point to protect the environment is to be out in it. For more details visit our website.

The Ramblers Holidays Charitable Trust

Unlike many tour operators we have our own trust through which RWH Travel’s profits are channelled back into a variety of outdoor, walking-related or environmental conservation projects in the UK. The focus of the Trust’s financial support is Britain’s leading walking charity, The Ramblers, and their role in promoting the benefits and importance of walking to the British public. In addition the Trust welcomes applications for small grants from local organisations in the UK who need support for walking-orientated activities. This includes the establishment of footpaths and bridleways, funding for rebuilding bridges and renovating huts, as well as bursary funding for the Duke of Edinburgh’s Award for children who could not otherwise afford to do it. Please visit the ‘About Us’ section of our website and click on the Charitable Trust link for more details.

Heart and Sole

We appreciate that we are in a fortunate position to be able to use our profits to help make a difference to people's lives. Heart & Sole is a venture managed by our office staff, whose aim is to reach the heart of the communities in the countries we visit. Through Heart & Sole, we hope to make more of a long term, direct impact to these communities, particularly in less developed countries where even a small amount goes a long way. See our website for more information and details of some of the projects we support.

Staying In Touch

Mobile Phones

Please do provide us with a mobile phone contact number. We will only use this to contact you with important information relating to your holiday arrangements. 

Do keep your mobile phones switched on and readily available when travelling to the airport or if delayed in transit so that we can contact you with any last minute information relating to your travel arrangements.  

As a matter of courtesy, please switch off your mobile phone during walks, or endeavour to minimise its use. Please also try to minimise the use of mobile devices during group meals.


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