Cleveland Way

“Combine moor & Coast, abbeys & smuggler’s villages in an orgy of history & beauty on the Cleveland Way”

(109 miles, 7/10 days)

Well Waymarked
Well Waymarked

The Cleveland Way is a cracking ‘little’ long distance trail taking in great chunks of moorland and cliff edge walking and to a lesser extent the rivers which carve deeply in to the high moorland plateau. I say ‘little’ but that does not mean that it is either worthy or a big effort, just compared to the Coast to Coast and Pennine Way it is shorter . However it is wonderfully planned and visits nearly all the sites and scenes which typify the North York Moors. It is true that once you have done the Cleveland Way you have done the best of the North York Moors with its Coast.

The Route

The walk starts in the centre of the attractive market town of Helmsley. After passing through 60 odd miles of wild upland moors and hills the route drops down to the sea at Saltburn and spends its final 40 miles taking the cliff top path to a finish at Filey. It is this contrast which makes the Cleveland Way totally unique. No other long distance path combines moor and coast so successfully.

There is no time of the year when it is better or worse, just different. In fact walking the moors in winter is a real feel good experience.

Upper Farndale
Upper Farndale

Most Popular Itinerary

Day 1

Helmsley to Sutton Bank 11.5 miles.

An easy and relaxed start to the day so a visit to Rievaulx Abbey can easily be included (and should be). Starting after lunch it is also possible to visit the White Horse at Kilburn (where the limestone has been exposed in the shape of a horse) and ‘hop’ up Hambleton Hill.

Day 2

Sutton Bank to Osmotherley 12 miles

A high level walk over the escarpment of Sutton Bank all the way to Osmotherley. The views to the west are far reaching and the walking easy on excellent paths and old drove roads. Take a sandwich as there is little in the way of stops before dropping in to the busy little village of Osmotherley.


Day 3

Osmotherley to Great Ayton/Kildale 20.5 miles

Day 3 is sometimes split in two but if you are reasonably fit it is best to carry on all the way to Kildale (limited accommodation) or Great Ayton. The route is often described as a roller coaster of moorland walking as there are a number of times that the route drops a few hundred feet to a road or a pretty stream. The moors are windswept but the views are continually impressive and the walking usually easy with the worst sections of paths now flagged.

The hamlet of Chop Gate is where there  is some accommodation for an extra night.

Day 4

Great Ayton/Kildale to Saltburn 14.5 miles

Whether starting at Kildale or Great Ayton the first stop is Captain Cook’s spectacular obelisk style monument and a few miles further on the most iconic peak in the North York Moors, Roseberry Topping. Even though the Cleveland Way does not pass over the summit it is worth the detour. From here the track enters farmland and some woodland with the scents of the sea a constant backdrop. The Victorian seaside resort of Saltburn marks the start of the coastal section of the Way.

Roseberry Topping
Roseberry Topping

Day 5

Saltburn to Runswick Bay 13 miles

The initial stretch of coastline to Skinningrove is crumbling away quite dramatically. After Skinningrove the coastal path climbs steadily up Boulby Cliffs, the 2nd one being the highest cliff in England. The pretty fishing village of Staithes is next, a step back in history before another climb leads towards the final destination of the day, the incomparable Runswick Bay.

Day 6

Runswick Bay to Robin Hood’s Bay 11.5 miles

Cliff top walking from Runswick Bay and Port Mulgrave will be complemented during the morning with the large beach at Sandsend. Whitby is an excellent lunch stop with a short climb leading to the spectacular ruins of Whitby Abbey. From here to Robin Hood’s Bay is 6 miles of interesting walking past the lighthouse and old radar stations of the 2nd World War.

Whitby crab baskets
Whitby crab baskets

Day 7

Robin Hood’s Bay to Scarborough 14.5 miles

Robin Hood’s Bay is a dramatic sweep of sand but the path soon takes to the cliffs at Ravenscar. From here the walking is excellent and the views constantly impressive with the only serious drop being down to the peculiar buildings of Heyburn Wyke. Back on the cliffs Scarborough can be seen in the distance. The path undulates before arriving at the bright lights and popular sea front of this large seaside town. The end should be here but it is not!

Day 8

Scarborough to Filey 10 miles

A simple half day will take you down to the twin resort of Filey. The walking is ok but a little disappointing after the spectacular days before but milestone 103 is soon found and the walk officially finishes.

Filey Brigg
Filey Brigg


Cleveland Way map

O/S Maps OL 26 and OL 27 cover this walk.

Places to Stay

Church House Farm B & B, Danby

Raven Hall , Ravenscar

Personal Journey

I have to be honest and admit that I did not walk the Cleveland Way in one continuous journey but broke it up in to segments, many fitting in to individual walks, sometimes circular in nature. However what I can say is that I walked every step with only the coastal 10 miles from Scarborough to Filey not yet done. The rest of the coastal stretch I did in 2 days and then enjoyed the ‘inland’ sections on a variety of multi day walks. And it was great but harder work than I thought it would be.

Forget your thoughts that the North York Moors is just and upland moorland plateau which you walk around in an airy but flat manner. It is not. Only on the stretch between Helmsley and Osmotherley is there any more than a mile of flat walking. The remainder is a constant round of climbs and descents which can be brutal. I found this particularly so on the coastal section north of Whitby. Hard work.

The Paths

However to compensate the paths are good and more pleasant on the feet than some of the other long distance paths. Mud may be encountered on the farmlands around Guisborough but overall it is not too bad. Both the Dales Way and the Cumbria Way are considerably worse for this. A major reason for this is that the Cleveland Way spends a good deal of its time on the higher land around rather than the lower valleys where conditions are often worse.

Mist my border collie came with me and it is certainly a more dog friendly long distance trail than many. There are enough dog friendly places to stay but more importantly the wide open spaces on the moors and the coastal path are brilliant for her to race around and not offend any land owner. The major danger appeared to be losing her off the crumbling cliff edge but the same could be said for myself!.

I have tried to fit the walks I did in to the Day by Day itinerary below and it certainly works most of the time.


Day 1.

From Helmsley to Sutton Bank 10.5 miles

This is a straightforward and short walk and can easily be left till after lunch but I would recommend a couple of slight detours. The first of these is Rievaulx Abbey which is half a mile off the route and the second is just short of Sutton Bank and the White Horse. Kilburn itself is a great place to stop for the night so the ‘horse’ may start you off on day 2!

Day 2.

From Sutton Bank to Osmotherley 12 miles 

Dominated by the far reaching views to the west I was lucky enough to be walking on a good day. The first section of the walk past the White Horse and Sutton Bank itself is described here . From here the ridge keeps to a steady height, passing Hambleton Hill (1309′) before gradually descending in to the ‘walking centre’ of the Moors, Osmotherley. There is a good choice of places to stay here, including a youth hostel. However I am bias, my brother lives here so the bed was good as was the food (and cheap!)

Day 3.

From Osmotherley to Great Ayton (20/22 miles)

Many break this in to 2 days but I just loved the long long days of upland moorland and this is a classic. From Osmotherley I soon joined the Lyke Wake Walk/Coast to Coast routes, all of which enjoy the lovely walking on the north west section of Moorland. The views are again good (even Middlesborough looks ok) and the walking excellent. If you do not believe me look at the pictures that are attached here  . Clay Bank offers an obvious break and the ‘bikers cafe’ is superb. The walking is hard in the initial section and I certainly felt I deserved it.

Kildale is enroute and still in the moors but it is quite straightforward to let gravity pull you down in to the larger town of Great Ayton.

Day 4.

From Great Ayton to Saltburn by the Sea (14.5 miles)

A day contrasting with the previous. Lowland walking predominates. Start though with a visit to 2 iconic land marks of the North York Moors, Captain Cook’s Monument and Roseberry Topping, Roseberry Topping is just skirted by the official route but is a great little summit, totally out of character with other higher points so far passed. From here there is, for me anyway, a rather uninteresting section around Guisborough with some farmland leading in to a wooded glade and the final miles to Saltburn. However the sea air and seagulls certainly changes the whole flavour of the walk.

Saltburn by the Sea has character and has retained some of its charm that made it such a popular holiday spot for the Victorians. Not many are better and some are considerably worse!

The next section is along the coast and because I like staying in the smaller places (rather than Whitby and Scarborough) some of the mileages are a little odd. It is perfectly possible to break the walk in to 4 days (2 getting you to Whitby and 2 from Whitby) but I prefer 3 with a break at Ravenscar and Robin Hood’s Bay.

Day 5.

From Saltburn to Runswick Bay (14 miles)

Ample time to enjoy my favourite part of the coast. There is a good deal of climbing to be done including that up to Boulby Cliff, the highest cliff in England. From Saltburn to Sinningrove the cliff is crumbling and the old railway about to be lost so take care. After Sinningrove the views are spectacular and dramatic, coastal walking at its best. Before you know it drop in to the old fishing village of Staithes for an explore and a lunch stop on the harbour walls. I have returned to Staithes a number of times and it really is an historical masterpiece but the Cleveland Way walker has not too much time to tarry and must carry on!

Another 5 miles brought me to Runswick Bay, a beautiful spot on a wide sweeping bay. A place to sit and ponder and enjoy the tranquility of the coast and ruminate on smugglers past. To me the best day on the coastal section of the walk.

Day 6.

From  Runswick Bay to Robin Hood’s Bay (13 miles)

Another busy day that defies the shorter mileage. The lure of Whitby on the first section of coast is strong but do not rush it. The coast is an orgy of fascinating coves, rocks and moonscape. It was unlike anything I had come across before until I dropped down to the more traditional sea side resort at Sandsend. Whitby is a great place to explore with its harbour, abbey and winding cobbled streets but take a  vow to come back and strike on towards Robin Hood’s Bay.

The steep pull up to the abbey from Whitby centre is the start of some straightforward walking. The views contrast with snippets of history to keep the enjoyment levels high. The path visits the Whitby lighthouse and old WW11 air raid radar posts. These are explained, along with other gems, by various notice boards enroute, an educational feature that the Park itself should be proud of and keen to maintain. Robin Hood’s Bay offers a fine place to stay the night although it is possible to travel the extra mile (as they say, and this may be 2) to Ravenscar on its position perched high on the cliffs.

Day 7.

From Robin Hood’s Bay to Scarborough (15 miles)

For me the section to the south east of Ravenscar lacks the dramatic appeal of that further north but that is not everyone’s view. Maybe it is after a couple of days of excellent coastal scenery the appeal just starts to pall. However the walking is good and certainly the pub at Heyburn Wyke fascinating. After Hayburn Wyke the cliffs start to drop away as the bright lights of Scarborough come to dominate the views.

Day 8.

From  Scarborough to Filey (10 miles)

I am not quite sure why the walk does not finish in Scarborough but as I have not yet walked the final 10 miles to Filey my opinion is fairly worthless. When I do I will let you know.

  • Jo Bersee-Mills says:

    You can easily divide the sections further if you want/prefer shorter walks or if the weather is unfavourable. For example, Staithes to Runswick Bay is a short hop but a very lovely section that gives you a ‘taster’
    You can also get a bus/train from eg Scarborough to Whitby then walk back to your accommodation
    Enjoy !

  • Paulette Wright says:

    I am planning on doing the cleveland way with my little dog in school Easter holidays 2019…. anyone fancy joining me? Not camping, will do B&B’s

  • Philip Backhouse says:

    I completed the walk last Tuesday after 9 days of fantastic walking & scenery. However I do not recommend taking a dog unless you are absolutely sure their pads can take it, the moorland section is mostly hard-core & gravel which was very tough on Ted’s paws. He walked with me as far as Sleightwath (57 miles) where i had to call my wife to collect him, also plenty of sheep, ladders & tics to take into consideration if you plan on taking a dog.
    I would also think carefully about trying to walk the 20 miles between Osmotherly & Kildale / Great Ayton don’t forget the reason you’re doing this, it’s not a race take time out to enjoy the views, the peace & quiet and people you meet along the way.

  • Antony High says:

    What an amazing page this is

    Im considering doing the full walk in 7/10 – but do not want to camp

    Can someone please let me know which hotels / B&Bs can be accessed on the route and how best to walk the full length in terms of days / stays

    a pre walked plan with hotel stops would be really approciated

    many thanks


  • Deb Roxborough says:

    I’m planning to do a long distance walk (25 miles) for charity but am not very good at reading maps. As I am walking it on my own I would like to know if the Cleveland Way easy to follow using only the signs on route. I’m hoping to follow the stretch from Osmotherley to Kildale or Great Ayton.
    Thank you

    • Jonathan says:

      It is quite well signposted but really you should be able to use a map. I could not guarantee yu wont get lost!

  • mel leese says:

    Hello Jonathan.
    I am planning to walk the Cleveland way in early May 2018 using your itinerary.
    I am just a little concerned about the stretch you describe from Osmotherly
    to either Kildale or Great Ayton. which is 21 or 22 miles.
    You describe this section as easy walking and can be done by anyone of reasonable
    I am 59 and enjoy walking and hiking. I have completed numerous long distance walks including the Coast to Coast last year.
    How many hours would this section take, and importantly how demanding is it ?
    Thank you Mel

    • Jonathan says:

      It’s a long day but impossible to tell you how long it will take as I do not know how quickly you walk. There are a couple of steep climbs but relatively short, the walk tends to be rolling.It is on good paths so it is the distance which is the issue, not any demanding terrain.

  • basic essay says:

    This page definitely has all the information I wanted concerning this subject
    and didn’t know who to ask.

  • Sheila Wheatley says:

    We are in the process of doing the wonderful Cleveland way over moorland forest and dramatic coastline my 10 year old twin grandsons are doing this with me just arrived in Whitby now ready for the next leg of this epic journey .

  • Dave says:

    Is there any disadvantage to walking the Cleveland way starting in Scarboro and finishing in Helmseley ? Thanks

    • Jonathan says:

      Only 2 mainly. As a rule people like walking west to east so the sun (!!) is behind you and also their is a general perception that finishing along the coast rather than moors is better. The main reason though is all the baggage handlers only operate one way.
      Mind you I walked the Coast to Coast east to west…just being perverse and enjoyed it

  • sarah M says:

    I walked from Scarborough to Whitby last weekend Feb 17th 2017 wonderful weather I think the walk South to North is much the best with the sun on your back the views are much superior. In Scarborough the best place to start is by the Tunny sculpture down by the harbour and take the path up to the castle gate for a magnificent view through the High bridge under the Castle Gate then zig zag down to North Bay and just follow the coast it is impossible to get lost. From Ravenscar to Robin Hoods Bay it was all down hill so it only took just over an hour and was much easier than I had expected. it probably helped that the tide was out so the last bit was along the beach. Otherwise it is a long hilly walk with several punishing flights of steps, usually on National Trust land!

  • Mal B says:

    There is now a cafe @ High Paradise Farm on the Cleveland Way section 2.

  • J. Read says:

    The stretch of Cleveland Way between Hood Lane access and Hayburn Wyke is frequently being used by cyclists and occasionally horse riders, there are no signs or notices that state. It is only for walkers at these access points

  • Stephen gartland says:

    We did the walk from saltburn to Whitby, this coastal route has got to be one of the most beautiful walks you can do, the views where fantastic. The walk its self was very hard.but enjoyed every step.

  • Pip Retigan says:

    The pub at Heyburn Wyke was a wonderful stopping off point on our walk from Scarborough to Robin Hood’s Bay. Not to be missed.

  • Stephen Gamble says:

    I walked from Scarborough to the other side of Cayton Bay on 21 April 2015. I paint landscapes, including coastal scenery and can say that this is a very attractive stretch of coastline. The path goes up and down hill but is not what I’d call too strenuous and no aching limbs to speak of the following day. Not sure precisely where in Scarborough the Cleveland Way begins but the sign I picked up for the Cleveland way was as you enter a dip with overhanging trees, close to Holbeck Hill and South Cliff. At one point, you have to come out and walk along a road and rejoin the footpath again.

  • sally says:

    where is the starting point for the walk starting at scarborough

    • Jonathan says:

      If you do the Cleveland Way from the coast the start is on Filey Brig, a mile on the Scarborough side of Filey. There is an officially marked point for the finishing post though but most carry on to Filey itself.

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