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.

Trail running tours available

We also organise trail running holidays along this route. Find out more.

About this route

3 nights
23 miles
2nd January to 24th December
Includes Dog-Friendly Tours

From £390 per person

Cleveland Way Short Break

This short break takes in the first stretch of the Cleveland Way along the southwestern edge of the North York Moors. Beginning at the market town of Helmsley, the trail traverses a mixture of wooded dales, open fields and cliff edges, visiting such interesting landmarks as the ruins of Rievaulx Abbey and Roulston Scar, where the head of the Kilburn White Horse can be reached.

After passing through Sutton Bank, the trail follows more clifftops and high moorlands filled with heather, before reaching the stone village of Osmotherley and admiring views over the Gormire Lake below.

Available tours

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

Short breaks

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

Cleveland Way Short Break 3 nights, 2 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


Depart from Osmotherley 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
© Contours Walking Holidays Cleveland Way Short Break  map
Helmsley to Osmotherley
23 miles (36 km)
2nd January to 24th December

Holiday highlights

Following the western edge of the North York Moors and enjoying spectacular views stretching out towards the distant Pennines.

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

Strolling peacefully around the quiet village of Osmotherley at the end of your holiday.

What's included?

  • 3 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

Tour Facts

Total distance: 22.5 miles (36 km)
Duration: 3 nights, 2 days walking
Minimum daily distance: 10.5 miles (17 km)
Maximum daily distance: 12 miles (19 km)
Code: CLEVWSB Grade: Moderate
Season: 2nd January - 24th December
Start of holiday: Helmsley
End of holiday: Osmotherley

Route Profile

Cleveland Way Short Break 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, Teesside International and Newcastle.

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). The nearest rail station to the end of the trail (Osmotherley) is at Northallerton (8 miles away).

By Bus - There are no direct buses from Malton to Helmsley, so a taxi would be required. There is an infrequent bus service from York to Helmsley, Monday to Saturday only, but a taxi would be a much quicker option, and essential on a Sunday/in between buses. There is a bus from Osmotherley to Northallerton Monday to Saturday only, so a taxi would be required on a Sunday.

From London - Trains run from London Kings Cross station to Malton or York. From there a taxi/bus will be required to Helmsley.

Return To The Start - There are no viable public transport options for this journey, so the the easiest way to return to the start of the trail would be to take a taxi from Osmotherley to Helmsley.

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.