Cleveland Way

(109 miles, 7/10 days)

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General Overview

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

Buildings in Glaisdale

This 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.

Typical Moorland Walking

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

One of the other pleasures of the Cleveland Way is the ease of securing accommodation – with only a bit of planning and varying the length of each day’s walk it is straight forward to find places to stay and pubs to eat in on the walk. That does not mean they will be available mid August the day before but for a National Trail the availability of accommodation is very good.

Cloisters at the Rievaulx Abbey

A Sample Day by Day 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. Overnight will be in one of the villages near Sutton Bank such as Kilburn itself.

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. Hambleton End at 1.300 foot is the high point. Take a sandwich as there is little in the way of stops before dropping in to the busy little village of Osmotherley. Stock up at this point with a long day to come.

Osmotherley centre

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 or even 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. Lunch spots can be found, the cafe at Clay Bank being one, but this is a day to let yourself go and soak in the miles. My favourite.

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 visiting although take care of the sudden drop. From here the track enters farmland as it skirts Guisborough and the smell of the sea is upon you. Some attractive woodland is passed through before the Victorian seaside town of Saltburn is reached.

Womderful early morning steam

Day 5 Saltburn to Runswick Bay 13 miles

The initial stretch of coastline to Skinningrove is enlived by the crumbling cliffs and old railway which have an inevitability of clashing soon – and there will be only one winner! 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 eventually be left behind for some traditional beack walking at Sandsend. Whitby will do for lunch (a place to return on a later visit) and then a short climb brings you back up to the cliffside path with the spectacular backdrop 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

Cliffs near Saltburn

Day 7 Robin Hood’s Bay to Scarborough 14.5 miles

Robin Hod’s Bay is a dramatic sweep of sand but the path soon takes to the cliffs again on the steep climb up to the dramatic point at Ravenscar. From here the walking is excellent and the views constantly dramatic with the only serious drop being down to Heyburn Wyke through some pretty woodland. Climbing out of here Scarborough is spotted in the distance but the path rolls up and down before arriving at the bright lights and popular sea front. 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.

Whitby crab baskets



Places to Stay

Garbutt Farm. Cold Kirby

Church House Farm B & B, Danby

Streanshalh B & B. Robin Hood’s Bay

Raven Hall , Ravenscar

Useful Links

Walk the Cleveland Way: Accommodation, Attractions and Advice An excellent E Book guide from Sally Jenkins who wlked the Way on one of our holidays


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 their any more than a mile of flat walking, the rest is a constant round of up and down which can be brutal. I found this particularly so on the coastal section north of Whitby. Hard work to do this.

However to compensate the paths are clear and not overly eroded providing good walking and less hard on the feet than some Long Distance walks I had done before. 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 but I have also moved off the traditional approach when writing up long distance paths by including some day walks that are well worth doing and will offer a much better and deeper perspective of the area.


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 (and Helmsley does a nice 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 shy 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 past the gliding station and the refreshments which can sometimes be found at Sutton Bank. From here the ridge keeps to a good 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 although 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)

I will say first off that 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, well worth giving the ham sandwich a miss for the day. Also 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 Great Ayton

Day 4. From Great Ayton to Saltburn by the Sea (14.5 miles)

A completely contrasting day of mainly lowland walking which I find a relief after the higher moors of the day before. 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 segulls certainly changes the whole flavour of the walk.

Saltburn by the Sea has some 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. It all becomes very personal at this stage.

Day 5. From Saltburn to Runswick Bay (14 miles)

Ample time to enjoy my favourite part of the coast but there is a good deal of climbing to be done including over Boulby Cliff, the highest in England. From Saltburn to Sinningrove the cliff is crumbling and the old railway about to be lost so take care but 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 of the walk but there are a lot of ups and downs.

Day 6. From  Runswick Bay to Robin Hood’s Bay (13 miles)

Another busy day that defies the reasonable mileage. Lunch at Whitby does draw you on over the first section of coast but do not rush it. The cliffside is an orgy of fascinating coves, rocks and moonscape and was unlike anything I had come across before until I dropped downto the more traditional sea side resort at Sandsend. Whitby is a great place to explore with its harbour, abbey and winding cobbled streets but just 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 contrasting with snippets of history to keep the enjoyment levels high (the route passes 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 just that after a couple of days of excellent coastal scenery the variety is just not there. However the walking is good and certainly the pub at Heyburn Wyke fascinating but the imminent arrival of Scarborough for the night is less so. The coastal scenery though will keep you going (it certainly did me) but eventually the cliffs drop away and the bright lights of Scarborough beckon.

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.


  1. 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


  2. 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!

  3. 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

  4. 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.

  5. 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

  6. basic essay says:

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

  7. 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 .

  8. 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

  9. Dave says:

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

  10. 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!

  11. Mal B says:

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

  12. 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

  13. 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.

  14. 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.

  15. 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.

  16. 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.

  17. sally says:

    where is the starting point for the walk starting at scarborough

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