The Cleveland Way Path

Helmsley to Filey in 9 Days Walking With Your Dog Code: CL10D

We offer 3 different itineraries covering the whole route. The longer the itinerary, the shorter the distance you have to walk each day. Our 10 night itinerary can also be booked with dog-friendly accommodation. Please select the code ending D if you would like to bring your dog with you.

Please note that many of our accommodation providers in Scarborough and Filey now operate a minimum two night policy, therefore it is likely you will spend the final two nights of your holiday in the same location, either Scarborough or Filey, with a transfer between.

A dog friendly itinerary along the entire length of the route. One of four dog friendly choices on the Cleveland Way.

This 9 day (10 nights) walk is our recommended holiday taking in the whole of the Cleveland Way route. This walk allows you to walk the whole route at comfortable daily distances.

The way passes through two very distinct types of landscape; classic moorland with fantastic views over the Cleveland Hills and the rest of the National Park, to dramatic coastline running along the top of some of the highest sea cliffs in the country.

Please be aware it is only possible to start this walk with your first night on a Monday, Tuesday, Wednesday or Thursday. Starting on another day may be possible but subject to some additional charges for transfers or weekend rates. Please just ask for more information.

You may add rest days but this will affect the day of the week that you can start. Please ask us for information.

Prices do not include any charges made for dogs by the accommodation providers. These should be paid by you directly to them on arrival. The amount will vary depending which accommodations we book you into but the estimated cost for the 10 nights is between £40 and £45.

See more useful information about dog-friendly holidays here.

Miles Km
Day 1 Travel to Helmsley for your first nights accommodation
Day 2 Helmsley to Kilburn 11 18
Day 3 Kilburn to Osmotherley 13 21
Day 4 Osmotherley to Great Broughton then transfer to Great Ayton 11 18
Day 5 Transfer to Great Broughton then walk to Great Ayton 12 19
Day 6 Great Ayton to Saltburn-By-The-Sea 13 21
Day 7 Saltburn-By-The-Sea to Runswick Bay 12 19
Day 8 Runswick Bay to Robin Hood's Bay 14 23
Day 9 Robin Hood's Bay to Scarborough then transfer to Filey 14 23
Day 10 Transfer to Scarborough then walk to Filey 11 18
Day 11 Depart from Filey after breakfast

Helmsley to Osmotherley: Along the eastern edge of the moors

The first section of the Cleveland Way provides an easy woodland walk across the beautiful landscape of the Rye Valley, passing the ruins of Helmsley Castle and later the medieval Rievaulx Abbey. These ruins are among the most beautiful in England and the dense wooded valley of the river Rye provides a magnificent setting. The walk then rises gently to the flat limestone plateaux of the Tabular Hills. It is also worth allowing time to visit the Kilburn White Horse, just before Sutton Bank.

From Sutton Bank the walk is relatively flat, following the western edge of the Hambleton Hills overlooking the Vale of York. The views from Sutton Bank are breathtaking. From High Paradise to Black Hambleton the route follows the old road used by the cattle men (drovers) in earlier centuries. After Black Hambleton you drop down to the idyllic setting of Oakdale’s reservoirs, en route to Osmotherley.

Osmotherley to Kildale: Across the top of the North York Moors

This is the most strenuous section of the trail, as the route follows the northern escarpment of the moors, broken by a series of valley’s cutting into the uplands between Huthwaite Green and Clay Bank Top. The views are stunning over the coastal plain to the North and across the bleak moorland and deep valleys to the South.

After Clay Bank Top a steep climb leads up to Round Hill, the highest point on the route, where tremendous views can be enjoyed. The route then descends gradually to Kildale which is studded with signs of the past – waymarkers, boundary stones and burial mounds.

Kildale to Saltburn-by-the-Sea: Roseberry Topping and on to the Sea

The first part of today’s walk is dominated by an ascent of Easby Moor, to Captain Cook’s Monument, and then the moorland ‘Matterhorn’, Roseberry Topping. Although only 1000ft (300m) high, this distinctive conical hill is prominent in the landscape. From the top the views are excellent. Gentler farmland, woodland and a riverside path lead onto the coast at Saltburn-by-the-Sea.

Saltburn-by-the-Sea to Robin Hood’s Bay

From here on the route hugs the coastline, through historic fishing villages, over high cliffs and along windswept beaches. From Saltburn the route heads up Hunt Cliff and along a section of dramatic cliffs to the highest point on the east of England at Rock Cliff. This route takes you down to sea level on three occasions and through the pretty villages of Staithes and Runswick, ending at the fishing village of Sandsend.

Dramatic coast paths lead onto Whitby, with its fine harbour, fossil filled cliffs and old town connections with Bram Stoker’s Dracula! A visit must be made to the imposing remains of Whitby Abbey high above the town.
Whitby and Robin Hood’s Bay are separated by an easy cliff top walk.

Robin Hood’s Bay to Filey

Between Robin Hood’s Bay and Scarborough the route encompasses ever-changing scenery, with the Flyingdales Moor to the west and the North Sea to the east. There are three steep descents and ascents along this path, where the sea interrupts the cliff top walk.

The arrival into the seaside town of Scarborough will provide you with another type of scenery, with its grand beaches, swish hotels and traditional seaside entertainment!

On leaving Scarborough, notice the vibrant colours from the South Cliff as you make your way to the final cliff top trail. The view of continuous coastal cliffs continues from Cayton Bay until your final destination, Filey.


The route covers rolling countryside and moorlands, but not mountains. If you are a regular walker this route should be within your capability.

Terrain: A walk of two halves – the North York Moors are rolling, sometimes remote, and up to 300m/1000ft high . The coastal path follows the cliffs with frequent descents to coves and beaches.

What’s it like underfoot? On the whole the paths are well defined and maintained, but at times it can be rough underfoot with some muddy paths, so good footwear is essential.

How much up & down? There are climbs of up to 300m some of which can be quite steep, through the Moors section, and short, sometimes steep climbs from sea level along the coast.

Signposting: Generally good.

Navigation: Pretty straightforward, but you may encounter hill fog or low cloud on the North York Moors, so make sure you can navigate.

All Holidays
Accommodation Overnight Bed and Breakfast accommodation in selected hotels, farmhouses, village inns, guest houses and family B&Bs.Full English or Continental breakfast.
Guidebook A detailed guidebook with route information, maps, photos and background information.
Information of Services Along the Route A comprehensive Service Info sheet, including services such as cash points, banks, post offices, village shops, inns, cafes and taxis.
Maps Three 1:25000 OS maps covering the entire route (OL26, OL27 & OL301).
Personal Itinerary A personal itinerary setting out each overnight stop, including large scale maps of each accommodation, to ensure you find it easily.
Emergency Telephone Support If you get in to difficulties during your holiday, we are always available to help, even out of office hours.
12.5% discount at Cotswold Outdoors We will issue you with a 12.5% Discount Card valid at all Cotswold Outdoor stores, and online, for the whole year on confirmation of your booking.
Luggage Transport We will transfer your luggage between each overnight stop – if you leave your luggage at the accommodation when you set off in the morning, it will be moved on to your next B&B. You only need to carry a small day sack with the clothes and provisions you require during the day’s walk.
Packed Lunches
Provided for each day’s walking and recommended on this holiday as there will not always be a handy shop or cafe on the route.
Off Road Parking If you are travelling by car we can usually arrange off road parking for the duration of your trip. (There may be a small charge for this).
Arrangement of return transport We can also arrange your transfer back to your car, (or advise you when public transport is a better option)!
What’s not Included
Evening Meals Your evening meal isn’t included in the package, but we include full details and recommendations for each evening meal in your itinerary. You will normally be within walking distance of a pub and/or restaurant, or where there is good food available at the accommodation, we’ll book that for you. Allow about £20.00 per night.
Transport to the Start & Away from the Finish Have a look at the “Travel Info” tab above for suggestions. If you’re still struggling, get in touch and we’ll help you sort it out.
Travel Insurance Even if you are based in the UK travel insurance is worth having.

Good accommodation and friendly hosts are an essential part of any holiday. We understand this and go out of our way to find the best. We put a great deal of effort into hand picking our accommodation and matching it to individual customer requirements. As well as visiting the accommodation ourselves, we ask all our customers to complete a short evaluation on each night’s accommodation, which then gives us an insight into the day-to-day operation and lets us spot any potential issues before they become a problem.

We use a variety of accommodation. Over the course of your trip you might stay in a village inn, a bed and breakfast in a converted barn, a Victorian guest house, or on a working farm. In selecting the accommodation we look for helpful, friendly hosts with good quality, characterful accommodation close to the trail. Occasionally we may use a chain hotel.

We always try to arrange en suite accommodation, i.e. rooms with their own bathrooms for each night of your stay. However, in some of the more remote locations accommodation is limited and occasionally we may have to book rooms with shared bathrooms for one or two nights of your holiday, (especially if the booking is made at short notice), but we will always let you know if this is likely to be the case.

We are happy to book single rooms on our holidays but cannot normally book more than two for any one group. Single room bookings include a supplement.

Here are some examples of the accommodation we use along the Cleveland Way:

Carlton LodgeSituated in the 12th Century market town of Helmsley, Carlton Lodge is an excellent guest house, perfectly located for the Cleveland Way and providing quality accommodation. The breakfasts here are something special, with all ingredients sourced locally walkers are assured of an excellent start to their day. Visit their website

Set at the top of the hill, Manningtree is a former sea captain’s house built in 1897. Located close to the Cleveland Way and Coast to Coast, this B&B is popular with walkers and returning guests who are enchanted by the fabulous location and wonderful hospitality offered here. Visit their website

General travel information on the Cleveland Way area will be in your holiday pack including train and bus timetables where available.

Detailed instructions on getting to your first night’s accommodation by car, or on foot from the nearest train or bus station, will also be included in the holiday pack on individual accommodation maps.

To view train times please visit trainline where you can also purchase tickets in advance. For information on bus timetables please visit traveline

If you require secure car parking whilst walking this route, we can usually arrange this in Helmsley. To return to your car we recommend using a taxi transfer as the journey by public transport is not very convenient and takes a long time.

Getting There:
By Air: The nearest International Airport is Leeds Bradford (LBA) You can then travel by train to Malton (journey time 55 mins approx) and then bus to Helmsley (16 miles). You can also fly to Newcastle (NCL) or Manchester (MAN) – from either of these airports you can take the train to Thirsk, and then bus to Helmsley.
By Public Transport: From York train station take a train to Malton (journey time 25 minutes) where you can take a bus (or taxi) to Helmsley 16 miles away.
By Road: Helmsley lies on the A170 (Thirsk to Scarborough Road) 14 miles east of Thirsk, and 13 miles west of Pickering. It is also at the end of B1257.

Returning from Filey:
Taxi: If you wish to return to Helmsley at the end of your walk, it is a difficult journey by public transport. We would be happy to arrange a taxi for your return journey.
Rail: Regular train services operate from Filey to London Kings Cross via Scarborough and York and North to Edinburgh on the East Coast mainline.

Robin Hood's Bay

This picturesque village is a hidden gem on the East Yorkshire coast consisting of a maze of tiny streets with individual shops, cafes and pubs. Robin Hood's Bay has a tradition of smuggling (during the late 18th century smuggling was rife on the Yorkshire coast) and there is reputed to be a network of subterranean passageways linking the houses. The rocks of Robin Hood’s Bay play host to a wealth of Jurassic history and fossilling is a wonderful activity for people of all ages along the huge, unspoilt beach. Likewise, the thrill of finding your first crab or starfish in a rock pool is equally as pleasurable.


A small, attractive seaside town with a long history of fishing, Filey has a magnificent beach with dramatic views of the long black finger of Filey Brigg in one direction and the chalk headland of Flamborough Head and Bempton Cliffs in the other.  It is well worth taking an extra day here to visit the RSPB Reserve at Bempton Cliffs. The Reserve is home to around 200,000 nesting birds including gannets, guillemots and kittiwakes during the breeding season.  Just a short distance further along the coast is the magnificent Flamborough Head, one of the best–preserved chalk headlands in Britain and home to the oldest complete surviving lighthouse in the UK.

Prices GBP (£)
Accommodation, map & guidebook only £1200
with Luggage Transport £1344
with Packed Lunches £1299
with Luggage & Lunches £1435

Other Options

Extra Nights (per night) £90
Single Supplement (per night) £65
Solo Luggage Supplement (per day) £15