8 days

  Hike across the vast heather-covered heathland of the North York Moors.

 Admire the views from Roseberry Topping and the Captain Cook Monument.

  Enjoy the sea breeze as you walk along the Jurassic Coastal Cliffs.

  Visit the gothic ruins of Whitby Abbey, the inspiration for Bram Stoker’s Dracula.

  Enjoy deliciously fresh fish & chips in lovely Victorian seaside villages.

Self-guided walking holiday on the Cleveland Way

From Osmotherley to Robin Hood’s Bay

The Cleveland Way is a lovely hiking trail that takes in two very distinct landscapes in North Yorkshire: The North York Moors and the Cleveland Heritage Coast. On this week-long walking holiday, you will enjoy a perfect mix of stunning coastal paths and typically stark and atmospheric Yorkshire moors.

Starting in the quaint village of Osmotherley, the route first follows the boundary of the North York Moors National Park (the UK’s largest tract of heather moorland), before reaching the coast at Saltburn. From there, you turn south to walk along the stunning Yorkshire Heritage Coast. This is a dramatic clifftop walk, passing over Eastern England’s highest point at Rock Cliff.

The Cleveland Way is the second of the ‘National Trails’, dating from 1969. The experience of half a walk over hill and scarp edges and half along the hilly coastline of the Yorkshire seaside makes this a real stand-out walk in the UK. There is much to enjoy for those interested in history, those ‘collecting’ National Trails and for aficionados who wish to enjoy arguably the best Fish ‘n’ Chips in England at Whitby Bay! Apart from busy coastal towns such as Scarborough, it remains a tranquil area, bolstered and protected by the presence of the National Park, which comprises about 80% of the walk. Yorkshire’s rich heritage is evident in such structures as the 13th century Whitby Abbey, the Captain Cook monument and the old cliff tramway at Saltburn.

8 DAYS / 7 NIGHTS From €899 per person sharing*

*A single supplement charge will apply for solo walkers.


We use a variety of accommodation along the route ranging from bed and breakfasts to lodges, pubs and small hotels. They are run by walker friendly hosts offering en-suite or private facility rooms with a tasty breakfast to get you ready for the walk ahead. Further facilities such as washing and drying facilities, packed lunches and packed lunches are available in some accommodations.
MEALS The overnight accommodations are on a bed & breakfast basis. You will have a selection of cold and hot options to choose from each morning.

Packed lunches can be booked and paid for on arrival at your accommodation. They offer a good selection of sandwiches, snacks and drinks for you to take with you for that day’s walk. On a few sections you will also pass a café and/or shop but on many days you will not pass anything between the start and finish.

For evening meals you will have a variety of pubs and restaurants to choose from, or your accommodation will provide a tasty meal.

AVAILABILITY You can start any day, subject to availability, between April and mid-October.
7 x nights in selected accommodation
7 x breakfasts
Day 2: transfer from Clay Bank top to hotel in Great Broughton
Day 3: transfer back to Clay Bank top from Great Broughton
Luggage transportation
Detailed info pack with maps and route notes (1 per room)
GPS tracks
Service hotline
Flights & travel insurance
Transport to Osmotherley or from Robin Hood’s Bay
Lunches & dinners
Any other items not mentioned in the program
Additional nights
Single room supplement
DIFFICULTY / TERRAIN The difficulty level of this tour is rated as moderate overall. Most of the route follows well sign-posted footpaths, which generally have good surfaces and are easy to follow. The exception to this is along the coastal path, which, in some places, is overgrown and uneven underfoot. The amount of daily ascent and descent is moderate, with much of the walk being on level or gently sloping ground. There are a number of steep ascents along the section from Osmotherley to Urra Moor and at some places along the coast, but these are generally of no more than one or two hundred metres at a time.

Day 1: Arrival in Osmotherley, North Yorkshire

Make your own way to Osmotherley and settle into this attractive small town on the edge of the North York Moors National Park. There are nice pubs, a café, and a remodelled 15th century church with 12th century Scandinavian carvings. If you arrive early, then you have the option of a short circular walk to Cod Beck Reservoir or to Mount Grace Priory.

Overnight: Osmotherley in an old country inn.


Day 2: Osmotherley to Clay Bank Top

Distance: 21 km | Ascent: 779 m | Descent: 849 m | 5 hrs approx.

Your first walking day is perhaps the hardest day of the route, as you are ascending and descending over a succession of moors to Clay Bank Top. The views in reasonable weather are extensive. Today’s route is shared with the Coast-to-Coast Path and is a roller coaster ride of a walk in the Cleveland Hills beside the crags of Cringle Moor and the famous Wainstones.

You come off the ridge at Clay Bank Top and you will be transferred from the car park there to your accommodation in Great Broughton (included).

Overnight: Great Broughton.


Day 3: Clay Bank Top to Great Ayton

Distance: 15 km | Ascent: 594 m | Descent: 536 m | 4 hrs approx.

After a short transfer back to Clay Bank car park, you start the day with a steep ascent up onto Urra Moor and the highest point of the journey at Round Hill (454 m). You are now walking on exposed high moorland, following the line of the disused Ironstone railway line and drovers’ roads which were used in centuries past to walk livestock to markets in the surrounding villages. You descend to the remote hamlet and railway station at Kildale, before ascending once more to the Captain Cook monument.

Overnight: Great Ayton.


Day 4: Great Ayton to Saltburn

Distance: 24 km | Ascent: 296 m | Descent: 543 m | 5 hrs approx.

The walk continues through forests with a diversion to “Roseberry Topping” an outlying craggy hill. It is a steep climb, but the views on a clear day are outstanding. You walk across more moorlands, then through the Guisborough woods and steeply down to Slapewath. You can take the opportunity to fortify yourself with a pint of the local ale before walking the last 7 km to Saltburn-by-the-Sea. This small Victorian seaside resort / fishing village was once famed for salt making and smuggling! The town is connected to its pier far below by a water-balanced cliff tramway, the oldest of its kind in Britain.

You have now left the moors behind. The whole nature of the walk changes from here as you turn south-eastwards along the coast.

Overnight: Saltburn-by-the-Sea.


Day 5: Saltburn to Runswick Bay

Distance: 19 km | Ascent: 391 m | Descent: 356 m | 5 hrs approx.

Walk along successive dramatic cliffs, passing the highest point on England’s east coast at “Rock Cliff” near Boulby. The highlight of the walk today is the beautiful little fishing village of Staithes. The distinctive fishing boats at the quay are called cobles and the village has a proud seafaring history. The famous explorer Captain Cook grew up in the village and served his apprenticeship in a shop on the seafront. Unfortunately, that shop has long ago been swallowed by the sea!

The trail continues onto the picturesque, red-roofed village of Runswick Bay. With its sweeping, sheltered bay and Jurassic shale cliffs, this is a fossil hunter’s paradise!

Overnight: Runswick Bay.


Day 6: Runswick Bay to Whitby

Distance: 13.5 km | Ascent: 379 m | Descent: 380 m | 3 hrs approx.

Quite a short walk today, giving you the chance to have a good look round Whitby.

From Runswick, there is another clifftop section before reaching Sandsend, from where you walk along the beach into Whitby. This red-roofed town grew rich between 1750 and 1850 on fishing, whaling, mining and shipbuilding. Whitby is also famous for the atmospheric ruined Abbey, which towers above the village and which inspired Bram Stoker’s Dracula (there is a Dracula Trail in the town). Whitby is a functioning fishing harbour, with fresh fish landed daily. The fish & chips here are said to be the best in England!

Overnight: Whitby.


Day 7: Whitby to Robin Hood’s Bay

Distance: 11 km | Ascent: 321 m | Descent: 278 m | 3 hrs approx.

Your final walking day is also your shortest, giving you the opportunity for a leisurely breakfast and late start. The climb out of Whitby Bay involves 199 steps and takes you up to the old abbey ruins, and St Mary’s Church. The trail then follows the coastal cliffs once more, re-joining the Coast-to-Coast trail for the last few miles into Robin Hood’s Bay. This charming village drops steeply and dramatically down to the sea. The Bay Hotel is a good place to sit with a beer on the terrace, gazing out over the North Sea and reflecting on a wonderful week of walking!

Overnight: Robin Hood’s Bay.


Day 8: Departure from Robin Hood’s Bay

Your trip comes to an end after breakfast this morning. You can take a bus or a taxi to nearby Scarborough for onward travel.

Getting to Osmotherley

  The closest airport is Leeds/Bradford.
/ You can get to Osmotherley via bus or taxi from Northallerton – which is on main railway line from London and York. It is also connected to many cities and airports around the UK.

Getting from Robin Hood’s Bay

  When you reach Robin Hoods Bay, you can get a bus or taxi back to Scarborough which has a railway station with connections to York, Leeds, Mancheser, London, Edinburgh and other major UK cities.

You can reach both Manchester and Newcastle airports in just over 4 hours.

Cleveland Way walking holiday
Hiking trail on the North York Moors
Sheep on the North York Moors
Bluebells at Clay Bank Top
Roseberry Topping
View over the North York Moors National Park
The North York Moors, near Whitby
The old tram and pier in Saltburn-by-the-sea
Saltburn pier at sunset
Saltburn beach
The picturesque fishing village of Staithes on the Cleveland Coast
Staithes fishing village
Whitby village and abbey
Whitby seafront
Boats in the harbour at Whitby
St Mary’s Church, Whitby
The gothic ruin of Whitby Abbey
Saltwick Bay, Whitby
Robin Hood's Bay
Robin Hood's Bay

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