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

6 nights
58 miles
2nd January to 24th December
Includes Dog-Friendly Tours

From £735 per person

Cleveland Way - Moors Section

The North York Moors section of the Cleveland Way begins in Helmsley and takes in the UK’s largest expanse of heather moorland on route to Saltburn-by-the-Sea. The historic landmarks of Helmsley Castle and the ruins of Rievaulx Abbey are just some of the amazing sights nestled among beautiful surroundings here.

The breath-taking viewpoints of Sutton Bank and Roseberry Topping are worth pausing at to admire the views, while the many quaint settlements along the way offer warm welcomes and insightful history to explore at your leisure.

Available tours

Code Tour Duration Difficulty Price per person
CLEVWM From Helmsley to Saltburn-by-the-Sea 6 nights, 5 days walking Moderate £735

Short breaks

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

Cleveland Way - Moors Section 6 nights, 5 days walking

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

Travel to Helmsley where your first night's accommodation will be booked

Day 1

Helmsley to Sutton Bank(T). 10.5 miles (17km) / 1421 ft (433 m) ascent

Day 2

Sutton Bank(T) to Osmotherley. 12 miles (19km) / 1004 ft (306 m) ascent

Day 3

Osmotherley to Clay Bank Top(T). 11 miles (18km) / 2500 ft (762 m) ascent

Day 4

Clay Bank Top(T) to Captain Cook's Monument(T). 12 miles (19km) / 1421 ft (433 m) ascent

Day 5

Captain Cook's Monument(T) to Saltburn-by-the-Sea. 12 miles (19.5km) / 1414 ft (431 m) ascent


Depart from Saltburn-by-the-Sea 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 - Moors Section map
Helmsley to Saltburn-by-the-Sea
58 miles (93 km)
2nd January to 24th December

Holiday highlights

Spotting gliders from Sutton Bank, with outstanding views over the Vale of York.

Reaching the North York Moors’ highest point on Urra Moor with far reaching views across the Cleveland Way.

Arriving in the Victorian seaside resort of Saltburn-by-the-Sea and strolling along its pier, the most northerly surviving British pier.

What's included?

  • 6 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

The charming village of Osmotherley, with its neat stone cottages huddled around its green, ancient market cross and stone table where John Wesley preached during one of his sermon tours is a popular choice for an extra night. A lovely short walk from here visits the Lady Chapel and Mount Grace Priory, an attractive 14th century Carthusian monastery.

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: 58 miles (92.5 km)
Duration: 6 nights, 5 days walking
Minimum daily distance: 10.5 miles (17 km)
Maximum daily distance: 12 miles (19.5 km)
Code: CLEVWM Grade: Moderate
Season: 2nd January - 24th December
Start of holiday: Helmsley
End of holiday: Saltburn-by-the-Sea

Route Profile

Cleveland Way - Moors 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 Airport, Manchester and Teesside International.

By Rail - The nearest rail stations to the start of the trail (Helmsley) are either Malton (about 16.5 miles away) or York (about 25 miles away). There is a rail station at the end of the trail (Saltburn).

By Bus - There are no direct buses from Malton to Helmsley, so a taxi would be required. There is a rather infrequent bus service from York to Helmsley, Monday to Saturday only, but a taxi would be a much quicker option, and essential on Sunday/in between buses. Various bus services run from Saltburn-by-the-Sea.

From London - Trains run from London Kings Cross station to Malton & York. A taxi/bus will then be required to Helmsley.

Return To The Start - To easiest way to return to the start of the trail is to take a taxi, as public transport options take much longer.

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 - Moors Section

“I found the walk very interesting particularly the views across to the Pennines. I found the selection of B&B's very good and would certainly recommend your company to others.”
Mr Wood, UK
“A brilliant walk arranged by yourselves of course and helped by perfect walking weather, all the accommodations were good. Once again thanks for a great holiday and let us know when we need to book for next April.”
Mr Bottomley, UK
“I appreciated the efforts made to cut down the daily mileage- my husband managed well and thoroughly enjoyed the holiday.”
Ms Angus, UK
“5 similar distance walking days, with extensive views throughout, blessed for the most part by dry, sunny weather. Well organised, as always. We've been using Contours every year since 2010!”
Mr Parkinson, UK
“For most of the walk I just had sheep and Grouse for company. It was isolated and beautiful.”
Mrs Davies, UK
“Beautiful scenery. Certainly an undulating walk, strenuous in parts. Very helpful to have roughly equal distances each day. A very interesting five-day walk in beautiful countryside.”
Mr Donnelly, UK
Find your holiday