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Overview

Walking Holidays
10 - 11 Nights
109 miles / 176 km
  • Prices from: £865 per person
  • Start: Helmsley, North Yorkshire
  • Finish: Filey, North Yorkshire
  • Availability: Any start date from March to October
  • Grading: Moderate
  • Way-marked: Yes

Cleveland Way Highlights

Contrasting scenery
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Experience a superb walk of complete contrasts – wild moorlands, dramatic cliff tops and superb coastal views.

North York Moors National Park
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Enjoy the spectacular views and abundant flora and fauna of North York Moors National Park; from the wonder of ancient trees to stunning wild birds of prey.

Captivating abbeys
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Visit the remains of the splendid Rievaulx Abbey and the gothic 13th century Whitby Abbey.

Robin Hood's Bay
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Explore Robin Hood’s Bay, a delightful heap of cliff-hanging cottages clinging to steep slopes and smugglers’ hideouts.

Captain Cook Monument
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Visit the Captain Cook Monument in Great Ayton. This impressive memorial commemorates one of the finest sailors and greatest explorers of all time who learned his craft in nearby Whitby.

Beautiful Staithes
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Enjoy panoramic views of the colourful harbour village Staithes, one of England’s most picturesque villages, full of quaint cottages and winding streets.

A Walk of Contrasts Through Glorious North Yorkshire

The Cleveland Way follows a route of 110 miles through beautiful landscapes, ever-changing scenery and charming seaside towns of North Yorkshire. The contrast between the open heather-clad moorlands and the high coastal cliffs means that the trail is essentially two completely different walking experiences.

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Opened in 1969, the Cleveland Way begins in the attractive market town of Helmsley, before heading across the spectacular heather moorland of the North York Moors National Park, where it reaches the coast at Saltburn-by-the-Sea.

It offers magnificent coastal walking along the dramatic and rugged North Yorkshire and Cleveland Heritage Coast to the seaside town of Filey, passing through beautiful, old fishing villages and lively coastal towns on the way. An understandably popular walk, the Cleveland Way has copious things to see and do along the way, as each town or village has its own local history, culture and hospitality.

Between the 900 year old Helmsley Castle, the bustling harbour of Whitby and the smuggling secrets of Robin Hood’s Bay, the unique identity and heritage of the North York Moors shines through with every footstep.

Cleveland Way Route Map

Recommended Itinerary

Our most popular itinerary is CW1 which covers the route in 9 days / 10 nights.

Travel to Helmsley for your first night’s accommodation
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Arrive in Helmsley, a pleasant market town, and spend the evening at your first night’s accommodation.

Day 1: Helmsley to Sutton Bank (10 miles / 16 km)
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The Cleveland Way begins in Helmsley. Your first days walk is fairly easy, across the beautiful landscape of the Rye Valley where a short detour takes in the ruins of splendid Rievaulx Abbey.

The route then climbs onto the flat plateau of the Tabular Hills to Hambleton Hill, before it descends into the hamlet of Sutton Bank with views over the distant Pennines. Allow time to visit the White Horse of Kilburn, a limestone horse carved into the hillside on the way.

Day 2: Sutton Bank to Osmotherley (11 miles / 17.5 km)
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From Sutton Bank the walk traces the western edge of the North York Moors National Park and the views are truly breathtaking. Follow part of the Hambleton Drove Road for a few miles; an ancient upland thoroughfare, before the climb up to Hambledon End; at 1309 feet, the high point of the day. There are great views from the ridge before the route descends to the charming village of Osmotherley with its quaint shops, cafes and pubs.

Day 3: Osmotherley to Clay Bank Top (11 miles / 17.5 km)
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This section of the Cleveland Way is remarkably hilly, a roller-coaster of a walk up and down the Cleveland Hills and the most strenuous section of the route. On a clear day this is a very scenic and beautiful stretch providing stunning views over the coastal plain to the North and across the bleak moors to the South. Your accommodation tonight is in the village of Great Broughton located 2 miles off the trail.

Day 4: Clay Bank Top to Cpt Cook Monument (11.5 miles / 18 km)
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This is the most remote section and across the highest part of the North York Moors. Climb over Urra Moor to the summit of Round Hill, at 1489 feet the highest point of the route and enjoy sweeping views. In calm, clear weather this is one of the most memorable parts of the route, however on a bad day the moors can be windswept and inhospitable.

From Tidy Brown Hill the route descends through Battersby Moor into the village of Kildale. Continue on from Kildale and the Cleveland Way now enters Captain Cook country. The route climbs up Easby Moor to visit Captain Cook’s Monument, born nearby in 1728.

 

Day 5: Cpt Cook Monument to Saltburn-by-the sea (12.5 miles / 20 km)
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A few miles further on from the Captain Cook’s Memorial, the route takes a steep climb up the eroded sand stone stump of Roseberry Topping, the ‘Yorkshire Matterhorn’ – although only 1000ft high, this distinctive conical hill is prominent in the landscape.

The bustling town of Guisborough can be seen, but the Way passes high above it over Guisborough Moor and onto the gentler farmland leading to the coast and the Victorian seaside resort of Saltburn.

Day 6: Saltburn to Runswick Bay (12 miles / 19 km)
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From Saltburn the Cleveland Way enjoys its first day along the coast, taking in splendid cliffs and coves. Head up Hunt Cliff and along a section of dramatic cliffs. There are several stiff climbs on this section of the walk and you will be climbing up around 1000 feet – the second cliff at Boulby is the highest on the East coast of England. In between the hills however the route descends to sea level losing all the height you have gained!

From Boulby descend to the charming and colourful harbour village of Staithes. Visit the excellent Captain Cook and Staithes Heritage Centre. The cliff coast continues to Runswick Bay, another delightful little village situated on a steep slope facing the bay.

Day 7: Runswick Bay to Robin Hood's Bay (15 miles / 24 km)
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From Runswick Bay follow the dramatic coast path to Sandsend before enjoying an easy stroll to Whitby; probably the most special town along the route with its Old Town, fine harbour and fossil filled cliffs. Most walkers want some time to explore the narrow streets and bustling harbour-side of this old whaling town.

Whitby and Robin Hood’s Bay are separated by an easy cliff top walk. Arrive in Robin Hood’s Bay, a delightful heap of houses clinging to steep slopes.

Day 8: Robin's Hood Bay to Scarborough (14 miles / 22 km)
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Leave Robin Hood’s Bay and from here to Scarborough the scenery changes continually, with Flyingdales Moor to the west and the North Sea to the east. The route follows a roller-coaster path along the cliffs and this section is a lovely peaceful walk. Ahead lies the busy seaside town of Scarborough with its grand beaches and traditional seaside entertainment!

Day 9: Scarborough to Filey (12 miles / 19 km)
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Away from the bustle of Scarborough the final leg of your Cleveland Way walk takes you out along the esplanade above South Bay where you could visit the old castle and spa complex and enjoy some of the town’s history and heritage before you leave.

The view of continuous coastal cliffs continues as you enjoy easy walking on the cliff paths until your final destination, the small fishing town of Filey.

Onward travel
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After breakfast, you will start your journey home after a wonderful walking holiday on the Cleveland Way.

What’s Included?

Your Cleveland Way walking holiday includes:

  • Carefully selected accommodation along the route and trail transfers when applicable
  • En-suite or private bathroom facilities whenever possible
  • Daily door-to-door baggage transfers
  • Comprehensive information pack, kit list, guidebook and map (one set per room)
  • Personalised itinerary with details of your accommodation, route and recommendations for lunch and dinner
  • Traditional English breakfast
  • 24-hour emergency contact number
  • Full financial protection

Your walking holiday doesn't include:

  • Travel insurance
  • Transport to and from the start and end of the walk
  • Lunches and evening meals

Itineraries & Prices

We offer 4 suggested itineraries for walking the Cleveland Way.

Our most popular itinerary is CW1 which covers the route in 9 days. We also offer the Cleveland Way as 2 highlight packages, each of which is an excellent walk in its own right. This gives those with less time the opportunity to complete the trail in 2 stages.

Tour code
Itinerary
Average miles infoAverage miles per day
Difficulty infoLevel of difficulty
Price per person
CW1
9 Days / 10 Nights
12 miles per day
Moderate
From £865
Average miles infoAverage miles per day 12 miles per day
Tour code: CW1
Difficulty infoLevel of difficulty Moderate

9 Days / 10 Nights (CW1)

This itinerary lists our preferred overnight stops for this package. Transfers are included when you are staying away from the trail.

Additional nights can be added at any stage along the walk and we would be delighted to adjust it for you.

All of our prices are per person based on two people sharing a room. Our packages include all accommodation, baggage transfers and full information pack.

Single room & solo walker supplements

Single rooms are available at a supplement which covers the additional costs of a single room or single occupancy of a twin or double room.

  • Premium: £50 per night
  • Standard: £35 per night

As we incur additional costs for transferring a single bag there is a solo walker supplement of £10 per day in addition to the single supplement.

Arrive Travel to Helmsley for your first night's accommodation
1
Day 1 Helmsley to Sutton Bank 10 miles / 16 km
2
Day 2 Sutton Bank to Osmotherley 11 miles / 17.5 km
3
Day 3 Osmotherley to Clay Bank Top (overnight Chop Gate) 11 miles / 17.5 km
4
Day 4 Clay Bank Top to Cpt Cook Monument (overnight Great Ayton) 11.5 miles / 18 km
5
Day 5 Cpt Cook Monument to Saltburn-by-the-sea 12.5 miles / 20 km
6
Day 6 Saltburn-by-the-sea to Runswick Bay 12 miles / 19 km
7
Day 7 Runswick Bay to Robin Hood's Bay 15 miles / 24 km
8
Day 8 Robin Hood's Bay to Scarborough 14 miles / 22 km
9
Day 9 Scarborough to Filey 12 miles / 19 km
Depart Onward travel from Filey

Prices

Premium
Best available Guest Houses, Inns & Hotels
£1105 per person

Carefully selected guest houses, inns and hotels throughout your walk, which will be the best available in each location. As premium accommodation is in short supply on this trail, please note that some establishments will be of a higher standard than others. En-suite facilities or private bathroom guaranteed.

Standard
Good quality B&Bs, Guest Houses & Hotels
£865 per person

Good quality and comfortable B&Bs, guest houses and some hotels located as close to the trail as possible. We will prioritise en-suite facilities or a private bathroom, although in remote areas with limited accommodation this may not always be possible.

CW2
10 Days / 11 Nights
11 miles per day
Moderate
From £930
Average miles infoAverage miles per day 11 miles per day
Tour code: CW2
Difficulty infoLevel of difficulty Moderate

10 Days / 11 Nights (CW2)

This itinerary lists our preferred overnight stops for this package. Transfers are included when you are staying away from the trail.

Additional nights can be added at any stage along the walk and we would be delighted to adjust it for you.

All of our prices are per person based on two people sharing a room. Our packages include all accommodation, baggage transfers and full information pack.

Single room & solo walker supplements

Single rooms are available at a supplement which covers the additional costs of a single room or single occupancy of a twin or double room.

  • Premium: £50 per night
  • Standard: £35 per night

As we incur additional costs for transferring a single bag there is a solo walker supplement of £10 per day in addition to the single supplement.

Arrive Travel to Helmsley for your first night's accommodation
1
Day 1 Helmsley to Sutton Bank 10 miles / 16 km
2
Day 2 Sutton Bank to Osmotherley 11 miles / 17.5 km
3
Day 3 Osmotherley to Clay Bank Top (overnight Chop Gate) 11 miles / 17.5 km
4
Day 4 Clay Bank Top to Cpt Cook Monument (overnight Great Ayton) 11.5 miles / 18 km
5
Day 5 Cpt Cook Monument to Saltburn-by-the-sea 12.5 miles / 20 km
6
Day 6 Saltburn-by-the-sea to Staithes 9 miles / 14km
7
Day 7 Staithes to Whitby 11 miles / 17.5 km
8
Day 8 Whitby to Robin Hood's Bay 8 miles / 12 km
9
Day 9 Robin Hood's Bay to Scarborough 14 miles / 22 km
10
Day 10 Scarborough to Filey 12 miles / 19 km
Depart Onward travel from Filey

Prices

Premium
Best available Guest Houses, Inns & Hotels
£1220 per person

Carefully selected guest houses, inns and hotels throughout your walk, which will be the best available in each location. As premium accommodation is in short supply on this trail, please note that some establishments will be of a higher standard than others. En-suite facilities or private bathroom guaranteed.

Standard
Good quality B&Bs, Guest Houses & Hotels
£930 per person

Good quality and comfortable B&Bs, guest houses and some hotels located as close to the trail as possible. We will prioritise en-suite facilities or a private bathroom, although in remote areas with limited accommodation this may not always be possible.

CW3
5 Days / 6 Nights (Classic Moorland)
11 miles per day
Moderate
From £535
Average miles infoAverage miles per day 11 miles per day
Tour code: CW3
Difficulty infoLevel of difficulty Moderate

5 Days / 6 Nights (CW3)

This itinerary lists our preferred overnight stops for this package. Transfers are included when you are staying away from the trail.

Additional nights can be added at any stage along the walk and we would be delighted to adjust it for you.

All of our prices are per person based on two people sharing a room. Our packages include all accommodation, baggage transfers and full information pack.

Single room & solo walker supplements

Single rooms are available at a supplement which covers the additional costs of a single room or single occupancy of a twin or double room.

  • Premium: £50 per night
  • Standard: £35 per night

As we incur additional costs for transferring a single bag there is a solo walker supplement of £10 per day in addition to the single supplement.

Arrive Travel to Helmsley for your first night's accommodation
1
Day 1 Helmsley to Sutton Bank 10 miles / 16 km
2
Day 2 Sutton Bank to Osmotherley 11 miles / 17.5 km
3
Day 3 Osmotherley to Clay Bank Top (overnight Chop Gate) 11 miles / 17.5 km
4
Day 4 Clay Bank Top to Cpt Cook Monument (overnight Great Ayton) 11.5 miles / 18 km
5
Day 5 Cpt Cook Monument to Saltburn-by-the-sea 12.5 miles / 20 km
Depart Onward travel from Saltburn-by-the-sea

Prices

Premium
Best available Guest Houses, Inns & Hotels
£630 per person

Carefully selected guest houses, inns and hotels throughout your walk, which will be the best available in each location. As premium accommodation is in short supply on this trail, please note that some establishments will be of a higher standard than others. En-suite facilities or private bathroom guaranteed.

Standard
Good quality B&Bs, Guest Houses & Hotels
£535 per person

Good quality and comfortable B&Bs, guest houses and some hotels located as close to the trail as possible. We will prioritise en-suite facilities or a private bathroom, although in remote areas with limited accommodation this may not always be possible.

CW4
5 Days / 6 Nights (Heritage Coastal)
11 miles per day
Moderate
From £530
Average miles infoAverage miles per day 11 miles per day
Tour code: CW4
Difficulty infoLevel of difficulty Moderate

5 Days / 6 Nights (CW4)

This itinerary lists our preferred overnight stops for this package. Transfers are included when you are staying away from the trail.

Additional nights can be added at any stage along the walk and we would be delighted to adjust it for you.

All of our prices are per person based on two people sharing a room. Our packages include all accommodation, baggage transfers and full information pack.

Single room & solo walker supplements

Single rooms are available at a supplement which covers the additional costs of a single room or single occupancy of a twin or double room.

  • Premium: £50 per night
  • Standard: £35 per night

As we incur additional costs for transferring a single bag there is a solo walker supplement of £10 per day in addition to the single supplement.

Arrive Travel to Saltburn-by-the-sea for your first night's accommodation
1
Day 1 Saltburn-by-the-sea to Staithes 9 miles / 14 km
2
Day 2 Staithes to Whitby 11 miles / 17.5 km
3
Day 3 Whitby to Robin Hood's Bay 8 miles / 12 km
4
Day 4 Robin Hood's Bay to Scarborough 14 miles / 22 km
5
Day 5 Scarborough to Filey 12 miles / 19 km
Depart Onward travel from Filey

Prices

Premium
Best available Guest Houses, Inns & Hotels
£760 per person

Carefully selected guest houses, inns and hotels throughout your walk, which will be the best available in each location. As premium accommodation is in short supply on this trail, please note that some establishments will be of a higher standard than others. En-suite facilities or private bathroom guaranteed. 

Standard
Good quality B&Bs, Guest Houses & Hotels
£530 per person

Good quality and comfortable B&Bs, guest houses and some hotels located as close to the trail as possible. We will prioritise en-suite facilities or a private bathroom, although in remote areas with limited accommodation this may not always be possible.

Cleveland Way Accommodation

All of the accommodation that we reserve for you has been personally selected by our expert team to ensure it meets our exacting standards. We regularly review our extensive database.

We will always prioritise accommodation as close to the walking trail as possible. Occasionally, your accommodation may be located a short distance from the trail, or you may need to spend more than one night in the same place, in which case we will provide return transfers.

Travel Information

As an environmentally conscious tour operator, we actively encourage the use of public transport by providing clients with a detailed breakdown of travel options in their information packs. The following information may help with your pre-trip planning.

Getting to Helmsley
By Air

Nearest International Airport: Leeds/Bradford and Manchester International

An airport shuttle bus operates between Leeds/Bradford airport and Leeds Railway Station. There are train services from Leeds to Malton (journey time 50 min). 

There is also an hourly train from Manchester Airport to Malton, via York. The journey time is approximately 2 hours 30 min. 

From Malton, you can take a local bus (or taxi) to Helmsley, which is 16 miles away.

By Public Transport

Nearest Railway Station: Malton

There are regular train services from London Kings Cross to York (journey time 2 hours, from Manchester 1 hour 30 min and from Edinburgh 2 hours 30 min). From York, you can connect with a service to Malton (journey time 25 min).

York is also accessible by National Express coaches.

From Malton you can take a local bus (or taxi) to Helmsley 16 miles away.

By Car

If you plan to travel by car, you may be able to leave it in Helmsley for the duration of your holiday.

There is a car park on the north side of Helmsley close to the start of the Cleveland Way. 

Departing Filey
By Air

Nearest International Airport: Leeds/Bradford and Manchester International

From Filey, you can take a 20 min train to Scarborough, where you can connect to a train to Manchester Airport (via York). 

There is also a train service linking Scarborough and Leeds, and the airport shuttle bus connects Leeds railway station and Leeds/Bradford airport.

By Public Transport

From the end of the walk at Filey you can travel onwards by all forms of public transport as it is well linked.

Regular train services operate from Filey to Scarborough and York, from which there are regular train services to London Kings Cross (journey time 2 hours) and to Edinburgh (journey time 4 hours 30 min).

National Express coach services also serve York.

 

By Road

If you have left your car in Helmsley you will be able to return to it by using the bus service from Filey via Scarborough.

If you would rather travel to Helmsley and return from Filey by taxi, then we’d be delighted to provide you with the contact details of taxi companies who offer this service.

Additional Days

We would be delighted to arrange additional accommodation for you along the Cleveland Way.

You may wish to plan a rest day or have an additional night at any of the locations along the route which offer activities or sightseeing opportunities – we’ve made some suggestions below. Please request this when you make an enquiry.

Helmsley
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  • Visit this charming little Yorkshire town with its huge variety of individual shops
  • Explore the imposing ruins of the 900 year old Helmsley Castle and Helmsley Walled Garden, built in 1759, which sits beneath it.
Osmotherley
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  • Visit the attractive stone village with its cottages huddled around the green and stone table where John Wesley preached during one of his sermon tours
  • A lovely short walk visits the Lady Chapel and Mount Grace Priory, an attractive 14th Century Carthusian monastery
Whitby
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  • Visit the Captain James Cook Monument and Memorial Museum
  • Explore the ruined Gothic Abbey, the inspiration behind the horror classic Dracula 
  • Take a stroll along the attractive harbour, enjoy the many restaurants, pubs, bars and the best fish and chips in the British Isles
Robin Hood's Bay
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  • Explore the charming and curiously complex village with its history of smuggling
  • Visit the unique Robin Hood’s Bay Museum, with exhibitions of local history, where details of the many shipwrecks and historic rescues in the Bay are displayed, as well as a unique model of a smuggler’s house.
Scarborough
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  • If you fancy somewhere lively towards the end of your holiday consider the bustling seaside resort of Scarborough.
  • Stop by Scarborough Castle and learn about its 2,500 years of turbulent history.

Make an enquiry

Cleveland Way

Need something more tailored?
Contact us via email:
enquiries@absoluteescapes.com

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