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Cleveland Way - The Full Trail - 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 - Saltburn - 15 miles (24 kms)
Day 7 Saltburn-by-the-Sea to Staithes - 9 miles / 14 kms
Day 8 Staithes – Whitby - 12 miles / 19 kms
Day 9 Whitby to Robin Hood’s Bay - 7 miles / 11 kms
Day 10 Robin Hood’s Bay – Scarborough - 14 miles / 23 Kms
Day 11 Scarborough to Filey - 11 miles / 18 kms
  • Grade: Grade 2
  • Total Distance - 110 miles
  • Duration: 11 days, 10 days walking
  • Maps and itinerary provided
  • 10 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 - £400.00
  • Station pick up from Thirsk to Helmsley - £58.00 or Malton to Helmsley - £65.00 up to 4 passengers
  • Transfer back from Filey back to Helmsley - £116.00 up to 4 passengers, 4 to 8 passengers - £200.00
  • Solo Walker supplement - £510.00.00 (includes single room supplement) please call to book
  • GPS rental - £25.00

Cleveland Way - The full trail - 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 will be the start of the wonderful coastal section, wandering through pretty fishing villages, such as Staithes and Runswick before reaching Whitby the home of Captain Cook, this is where he learned his seafarer's trade. Whitby is also home of the great Whalebone Arch which is a reminder of the many men who went hunting for whale. In 1826 200 men were lost at sea when the Esk was shipwrecked in a violent storm.

You will pass through Robins Hood’s Bay before reaching the large seaside resort of Scarborough before finishing your journey in Filey.


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 ClayBank 11 miles (18 kms)
Day 5 - Clay Bank to Kildale - 9.5 miles ( 15 kms)
Day 6 - Kildale to Saltburn - 15 miles ( 24 kms)
Day 7 - Saltburn to Staithes - 9 miles ( 14 kms)
Day 8 - Staithes to Whitby - 12 miles ( 19 kms)
Day 9 - Whitby to Robin Hood's Bay - 7 miles ( 11 kms)
Day 10 - Robin Hood's Bay to Scarborough - 14 miles ( 23 kms)
Day 11 - Scarborough to Filey - 11 miles ( 18 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 - 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.

Day 7 Saltburn-by-the-Sea to Staithes - 9 miles / 14 kms

This morning after a hearty breakfast, you will be ready to start the day with an ascent up Hunt Cliff the start of this striking section of the Cleveland Way, coming to the highest point on the east of England, Rock Cliff.

The trail then dips down into the quaint fishing village of Staithes, once one of the largest fishing ports on the North-East coast.

Day 8 Staithes – Whitby - 12 miles / 19 kms

After a short walk you will reach the remains of the harbour of Port Mulgrave at the base of the Rosedale cliffs. Little remains here these days other than the subtle hint of past industry. After a wander along the cliff tops is Runswick Bay, one of Yorkshire Coast’s prettiest villages. With its sandy beach which was once full of brightly coloured fishing boats is now a known for rock pooling, coastal walks and its amazing views.

Passing through the fishing village of Sandsend a dramatic coast path leads onto Whitby, with its busy harbour, fossil filled cliffs and Whitby Abbey the inspiration for Bram Stoker’s Dracula.


Day 9 Whitby to Robin Hood’s Bay - 7 miles / 11 kms

Today will be a pleasurable day across the cliffs from Whitby to Robin Hood’s Bay with some spectacular views and scenery.
Walking past the lighthouse and old radar stations of the 2nd World War you will reach Robin Hood’s Bay.

Day 10 Robin Hood’s Bay – Scarborough - 14 miles / 23 Kms

Today is a more strenuous day, however the scenery is magnificent with outstanding views which make it worth all your efforts.

Leaving Robin Hood’s Bay, the path takes to the cliffs again on the steep climb up to the impressive point at Ravenscar. From here the walk will provide stunning views with a walk down to Heyburn Wyke through some pretty woodland. Climbing out of here you will follow the undulating path to the seaside town of Scarborough, with its vibrant entertainment, large sandy beaches and grand hotels.


Day 11 Scarborough to Filey - 11 miles / 18 kms

An easier day today but still with stunning view as the path hugs the coastline along the cliff tops.

The trail ends at Filey Brigg a spit of rock jutting out into Filey Bay. You will see a rock sculpture marking the end of the Cleveland Way.

With a final descent down onto the promenade and then up into the town into Filey. We can add an extra night if would like to have a night stay at the end of your trip. See supplement


(A) Bed and Breakfast accommodation (twin or double share basis).
(B) Route map, guidebook and trip notes specific to your trip, including
emergency contact numbers.
(C) Luggage transfers between accommodation.
(D) Any transfers to overnight accommodations listed.
(E) 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!


What is a Double, Twin and Single room?

Room descriptions

Double – One double bed for two people.

Twin – Two single beds each for one person.

Single – A room with a single bed in.

Can I add an rest day into my walking holiday?

Yes you can at any point, just get in touch and we can discuss the best options for this trip.

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.

Do you provide maps and a guidebook of the trail?

Yes we do, we provide the Harvey Map for this route and also more detailed maps to guide you to your accommodation each night. You also will receive detailed trip notes that we have compiled which has everything you need in it to really help you make a great walk into a holiday of a lifetime.

Cleveland Way - The Full Trail - Self Guided photo's

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