Cleveland Way

Cleveland Way

A self-guided walk around the North York Moors National Park and the Cleveland Heritage Coast.

3 to 11 nights
23-111 miles
Moderate to Strenuous

From £390 per person

Find your holiday

About the trail

Take a self-guided walking holiday along the Cleveland Way, a walk of stunning contrasts. Beginning in the old market town of Helmsley, the Cleveland Way traverses the western escarpment of the North York Moors to the coast at Saltburn-by-the-Sea, before following the Cleveland Heritage Coast to the Victorian town of Filey.

While walking through the Moors, the trail traverses woodland, green dales and heather moorland. This section is packed with historic interest, including the iconic White Horse of Kilburn. The coastal section then follows high cliffs, sandy bays and wooded wykes. Picturesque fishing villages pepper the trail, as well as the famous port of Whitby. Overall, the Cleveland Way is an incredible walking trail filled with intrigue and beauty.

We offer multiple holiday options along this trail. If you wish to experience the entire trail, simply select the first option from the list below.

Choose your route

  • This route includes dog friendly tour options Cleveland Way
  • This route includes dog friendly tour options Cleveland Way - Moors Section
  • This route includes dog friendly tour options Cleveland Way - Coast Section
  • This route includes dog friendly tour options Cleveland Way Short Break

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

About this route

4 to 7 nights
53 miles
Moderate to Demanding / Strenuous
2nd January to 24th December
Includes Dog-Friendly Tours

From £515 per person

Cleveland Way - Coast Section

The Heritage Coast Section of the Cleveland Way begins in the Victorian seaside town of Saltburn-by-the-Sea and follows the rugged cliffs to Filey. While the scenery throughout is beautiful, some of the best views can be seen from Boulby, the highest cliffs in England.

Locations of particular interest include Whitby, boasting amazing history, heritage and folklore, and the seaside resort of Scarborough, with its ancient castle providing panoramic views over the Yorkshire coastline. This walk, marked by picturesque fishing villages and with a wealth of maritime and literary history, is a fantastic part of the England Coast Path.

Available tours

Code Tour Duration Difficulty Price per person
CLEVWC1 From Saltburn-by-the-Sea to Filey 4 nights, 3 days walking Demanding / Strenuous £515
CLEVWC2 From Saltburn-by-the-Sea to Filey 5 nights, 4 days walking Demanding £635
CLEVWC3 From Saltburn-by-the-Sea to Filey 6 nights, 5 days walking Moderate £755
CLEVWC4 From Saltburn-by-the-Sea to Filey 7 nights, 6 days walking Moderate £875

Short breaks

Code Tour Duration Difficulty Price per person
CLEVWSB From Helmsley to Osmotherley 3 nights, 2 days walking Moderate £390

Cleveland Way - Coast Section 4 nights, 3 days walking

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Route profile
  • Travel info
  • Weather
  • Holiday Highlights

Important information

Please note that the Filey overnight stop is currently proving difficult to book. If you are looking to book this tour, a transfer to a nearby town, or an upgrade fee to expand the accommodation options available to more expensive properties may be necessary. Please note your preference in the additional info field at the end of the booking form, or contact us directly if you wish to go ahead.

This tour is available to book all year, however out of season from end of October to March, there may be a small supplement for luggage moves, which will be moved by taxi rather than the usual luggage courier.


Travel to Saltburn-by-the-Sea where your first night's accommodation will be booked

Day 1

Saltburn-by-the-Sea to Whitby. 20.5 miles (33km) / 2805 ft (855 m) ascent

Day 2

Whitby to Hayburn Wyke(L). 15 miles (24km) / 1913 ft (583 m) ascent

Day 3

Hayburn Wyke(L) to Filey. 17.5 miles (28km) / 2073 ft (632 m) ascent


Depart from Filey after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation in most cases; should your accommodation be further than this, transfers will be provided as standard if practical. A very limited number of stops will require you to travel on foot up to two miles off the trail, however these instances will be clearly communicated to you if applicable.

Further transfers may also be required due to some accommodations having a two-night minimum booking policy, especially at weekends.

Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£70.00 per person / per night
Single Supplement
£55.00 per person / per night

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night
Extra night (Saltburn-by-the-Sea)
Price on request
© Contours Walking Holidays Cleveland Way - Coast Section map
Saltburn-by-the-Sea to Filey
53 miles (85 km)
2nd January to 24th December

Holiday highlights

Admiring the extensive views from Boulby, the highest cliffs in England.

Wandering through the fascinating features of Whitby, including the whalebone arch, Whitby Abbey and St Mary’s Church.

Experiencing the many quaint fishing villages and lively coastal towns along this spectacular piece of Yorkshire coastline.

What's included?

  • 4 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

A popular choice for an extra night is the historic seaport of Whitby, which boasts an attractive harbour, atmospheric ruined abbey, Captain Cook Museum, Lifeboat Museum, Whitby Museum and St Mary's Church. The interior of this intriguing church was altered in 1612 to resemble the lower deck of a wooden sailing ship.

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night
Extra night (Saltburn-by-the-Sea)
Price on request

Tour Facts

Total distance: 53 miles (85 km)
Duration: 4 nights, 3 days walking
Minimum daily distance: 15 miles (24 km)
Maximum daily distance: 20.5 miles (33 km)
Code: CLEVWC1 Grade: Demanding / Strenuous
Season: 2nd January - 24th December
Start of holiday: Saltburn-by-the-Sea
End of holiday: Filey

Route Profile

Cleveland Way - Coast Section Route Profile

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air

The most convenient major city and international airports are Leeds-Bradford, Manchester and Teesside International.

By Rail

There is a rail station at the start of the trail (Saltburn) and also at the end of the trail (Filey).

By Bus

Various bus services run to Saltburn-by-the-Sea and from Filey.

From London

Trains run from London Kings Cross station to Saltburn.

Return to Start

The easiest way to return to the start of the trail, is to catch the train from Filey to Saltburn-by-the-Sea. However, journey times are lengthy and do fluctuate, especially at weekends, so another option would be to take the train from Filey to Scarborough. Then take a bus to Whitby, followed by another bus to Saltburn.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.

Customer reviews from the Cleveland Way - Coast Section

“Staithes, Robin Hood's Bay, Scarborough and Filey all delightful, and Contours served us typically well with accommodation, seemless luggage transfers, and flexibility when needed.”
Mr Jarvie, UK
“The holiday arrangements worked very smoothly with the baggage transfer, route details and selected accommodations. I would highly recommend this company for your dog friendly walking holidays.”
Miss Wilkinson, UK
“One of the best holidays we have had. Accommodation, owners, directions and locations all perfect. Many thanks. We will be using Contours again.”
Mr Pickup, UK
“In an itinerary that is complex and involving the schedule we experienced, it was very satisfying to see the whole experience well organised and your pack and information worked extremely well... I would use your services again. Overall, every accommodation provider... had a great welcome and their staff were all very good, friendly, attentive and very personable. Covid procedures were in all cases well documented and executed. Some places were more rigorous than others but we were very pleased to comply and conform, it gave us a feeling of confidence in the accommodation.”
Mr Perry, UK
“The scenery was beautiful at every turn and the weather a huge bonus (t-shirt and shorts weather late September) Having our baggage transferred each day was great and the variety of B & Bs we stayed in was interesting. Each day's walking featured different highlights.”
Mrs Simpson, UK
“A good time was had by all the group. Spectacular scenery and the arrangements were first class. A good route of moderate difficulty. Would suit experienced walkers. Arrangements worked well.”
Mr McCloskey, UK
“Stunningly beautiful walk, very enjoyable, would do it again.”
Ms Unwin, UK
“I was hoping this would be a good walk, but it far exceeded my expectations! Booking process was very smooth (as always)!”
Mr McDowell, UK
“Superb stretch of coastline and all the arrangements worked out well.”
Mr Simmons, UK
Find your holiday