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Cleveland Way – Moorland Section -self-guided

at a glance

Day 1 Arrive - Helmsley - Overnight stay
Day 2 Helmsley to Sutton Bank - 10 miles (16 kms)
Day 3 Sutton Bank to Osmotherley - 11.5 miles (17 kms)
Day 4 Osmotherley to Clay Bank - 11 miles (18 kms)
Day 5 Clay Bank to Kildale - 9.5 miles (15 kms)
Day 6 Kildale to Saltburn - 15 miles (24 kms)
  • Grade: Grade 2
  • Total Distance - 57 miles
  • Duration: 6 days, 5 days walking
  • Maps and itinerary provided
  • 5 Nights B&B (Twin Share Basis)
  • Available for solo walkers
  • Luggage transfers
  • Loan of GPS for holiday
  • Emergency back up
  • Holiday Options
  • Single room supplement - £200.00
  • Station pick up Thirsk station - £58.00 or from Malton - £65.00 up to 4 passngers
  • Transfer from Saltburn-by-the-Sea back to Helmsley - £116.00 up to 4 passengers
  • Solo Walker supplement - £302.00 (includes single room supplement) please call to book
  • GPS rental - £25.00

Cleveland Way – Moorland Section -self-guided

In 1969 the 109-mile Cleveland Way opened, this was the second National Trial in England and Scotland to open. The route is a walk of two halves. Starting in Helmsley on the edge of the North York Moors it crosses farmland, woods, and beautiful heather moorlands then following along the dramatic coastline finishing in the seaside resort of Filey.

The route for this trip will start at the historic market town of Helmsley crossing the North York Moors National Park, traversing the moorlands of the Hambleton and Cleveland Hills before arriving at the Victorian seaside town of Saltburn-by-the-Sea.

This section of the Cleveland Way has stunning vistas, wildlife, iconic landmarks, and heritage sites.

Day 1- Arrive Helmsley
Day 2 - Helmsley to Sutton Bank - 10 miles (16 kms)
Day 3 - Sutton Bank to Osmotherley - 11.5 miles (17 kms)
Day 4 - Osmotherley to Clay Bank - 11 miles (18 kms)
Day 5 - Clay Bank to Kildale - 9.5 miles (15 kms)
Day 6 - Kildale to Saltburn-by-the-sea - 15 miles (24 kms)

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Day 1 Arrive - Helmsley - Overnight stay

You will arrive at the picturesque market town of Helmsley for your first night’s stay.

Arrive by train, we can arrange a station collection from Thirsk or Malton (See supplement).

Arrive by car, there is limited on street parking available for the duration of your trip at no charge, or permits are availalbe to buy in Helmsley to park in the Cleveland Way Car Park .

The choice is yours!

Day 2 Helmsley to Sutton Bank - 10 miles (16 kms)

This morning after a hearty breakfast, you will start your day with a leisurely walk along the river Rye in the Sylvan Valley. The rest of the day will be gradually climbing the Hambleton Hills, do take time to take a short detour to visit The White Horse one of Yorkshire’s best-known landmarks before following Roulston Scar back to Sutton Bank Visitors Centre. You will have a short transfer back to your overnight accommodation in Helmsley.

Day 3 Sutton Bank to Osmotherley - 11.5 miles (17 kms)

Start your day by taking in the views of Gormire Lake, formed over 10,000 years ago, and the Yorkshire Dales to the West. Walking north along the escarpment you will join the historic Hambleton Drove Road, leading over Black Hambleton to Oakdale. From Oakdale you will continue to Osmotherley where your overnight accommodation awaits.

Day 4 Osmotherley to Clay Bank - 11 miles (18 kms)

You will start your day today from the Market Cross. Before climbing to Beacon Hill why not visit Mount Grace Priory or Lady Chapel both will incur a detour but worth visiting. Traversing the northern ridge of the North York Moors and crossing valleys makes for probably the most demanding section of the Cleveland Way. You will have a short transfer to your overnight accommodation.

Day 5 Clay Bank to Kildale - 9.5 miles (15 kms)

Today you will cross the highest point of the North York Moors. After your ascent to Urra Moor the track continues to Botton Head, the summit. Lying just north of the path is Round Hill which is the highest point of the North York Moors at 1490 feet (454m).
After crossing the Ura Moor you will reach Bloworth Crossing the remotest point of the entire Cleveland Way, once a railway crossing bringing ironstone out of Rosedale to serve the developing industries of Teesside and Durham.
Heading north you will drop down into the Kildale. You will be staying the vicinity of Kildale tonight, this might mean a short transfer.

Day 6 Kildale to Saltburn - 15 miles (24 kms)

Today you will make your way to the coastal town of Saltburn in Captain Cook Country, coming across references along the way to Captain Cook who grew up in Great Ayton.
Crossing the Esk Valley rail line heading north the views will open to the Easby Moor with the monument of Captain Cook rising 51 feet in Height standing at the top. After descending to Gribdale Gate you will ascend to Newton Moor then to Roseberry Topping known to many as the ‘Yorkshire Matterhorn’.
Heading east you enter Guisborough Woods. The longest stretch of forestry on the Cleveland Way. Why not stop in Slapewath for refreshments before the final stretch through Skelton and the delightful Saltburn Woods, before reaching the sea at Saltburn.
At the end of the days walking it is just a short walk to Saltburn railway station. Alternatively, if you have arrived by car, we can run you back to Helmsley to pick your car up. See supplement



(A) Bed and Breakfast accommodation (twin or double share basis).
(B) Route map and instructions specific to your trip, including emergency contact numbers.
(C) Luggage transfers between accommodations.
(D) Emergency back-up service from Shepherds Walks Holidays mobile telephone number.


(A) Any additional transfers not mentioned in the dossiers
(B) Cost of parking your car for the duration of your trip
(C) Personal clothing and equipment.
(D) Insurance
(E) Lunch and Evening meals.
(F) Single room option (if required, see single supplement).
(G) Pick up and drop off at airports.
(H) Other entrance fees into attractions and public transport costs not mentioned above.


The Shepherds Walks Representative will:

A) Be available should you have any problems during your trip
B) Arrange the transportation of your luggage.
C) Provide transfers as necessary to your car / station if specified in your booking or itinerary.

We are here to offer you the best holiday you could ever imagine and we aim to do this through the personal service that we offer.

Make your holiday run smoothly – We are here for you. Our sole objective is for us to help you. We are here at any stage of your holiday and even in the planning stages. We tailor things to your requirements, not those of the masses.

We don’t cut corners - 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.

We have personally walked all the trips we offer - We know exactly what you are going to embark on and can advise you on any aspects of your holiday over and well above what many of our competitors can.

Press choose to walk with us – Shepherds Walks Holidays are asked to deliver a very high percentage of the trips for journalists in the region. When the Tourist Boards are approached by a journalist wanting to visit the area who do they ask to provide their holiday or take them out walking? Shepherds Walks.

We have had press trips on all our routes and the articles speak for themselves.

Protected Holiday - All our holidays are protected through the operation of a Trust Account.

We are close at hand if you need us – We are a local business and if you need us at any time during your holiday just ask. If you are on a self guided trip we often will catch up with you, even over a drink one evening, just to make sure everything is going well. It’s better to iron out any little problems during your holiday, rather than hearing about them when you are back at home.

We enjoy great relationships with your accommodation providers and they will help us to help you

As we are literally on the doorstep we know the best places to stay. 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 they will go that extra mile to help us to help you whilst out on your route.

That is why Shepherds Walks has won awards and has helped people relax and totally enjoy their visit to this wonderful part of the country. We are willing to go that extra mile!


Do I need travel insurance?

If you are coming to the UK from overseas it is a condition of our tours that you are covered by medical and personal travel insurance that includes repatriation to your home country. If you are a UK resident medical and personal travel insurance is also recommended. If you have not organised appropriate insurance yet, please do so before you travel.

Do you move our bags for us on our walking holiday?

Yes, we move your bags for you everyday. You just leave your main bag at your accommodation and we will move it for you, so it will be at your next nights accommodation waiting for you.

You just carry your day pack.

Your baggage allowance for the trip is one main piece of luggage which should be preferably either a backpack/rucksack or sports bag, and one small daypack. Try to travel as light as possible. It is best to avoid large solid hardtop suitcases as these cause difficulties on transfer vehicles etc.

The larger piece of luggage will travel on the vehicle between accommodations and the daypack should be suitable for carrying any additional outer-layer clothing and items you will need on your walk during the day. As a general rule, we would recommend that your main piece of luggage shouldn't weigh more than 15 - 20 kilos.

What type of accommodation will we be staying in - self guided trip

The accommodation on the tours are in Inns, family-run hotels, and Bed and Breakfasts. We endeavour to provide en-suite accommodation.

Cleveland Way – Moorland Section -self-guided photo's

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