Cleveland Way

(109 miles, 7/10 days)

General Overview


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This is a cracking ‘little’ long distance trail taking in great chunks of moorland and cliff edge walking with lesser time spent beside 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 North York Moors with its coast. Every day brings a present surprise and much to see with names just rolling off the tongue; Rievaulx Abbey, Mount Grace Priory, Roseberry Topping, Robin Hood’s Bay to name just a few.

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.

I have suggested a couple of itineraries which will suit both the quicker walker and those wishing to take more time. For further information and booking your walk with us just follow this link

To book a Walking Break on the Cleveland Way click here

1. A speedy itinerary – starting at Helmsley

Day 1: Helmsley to Osmotherley (22 miles)

Day 2: Osmotherley to Kildale (20 miles)

Day 3: Kildale to Saltburn (14.5 miles)

Day 4: Saltburn to Runswick Bay (12 miles)

Day 5: Runswick Bay to Robin Hood’s Bay (15 miles)

Day 6: Robin Hood’s Bay to Scarborough (14.5 miles)

Day 7: Scarborough to Filey (10 miles)

2. A more leisurely itinerary starting at Helmsley

Day 1: Helmsley to Sutton Bank (10 1/2 miles)

Day 2: Sutton Bank to Osmotherley (12 miles)

Day 3: Osmotherley to Clay Bank (11 miles)

Day 4: Clay Bank to Kildale/Great Ayton (9 miles)

Day 5: Kildale/Great Ayton to Saltburn (14.5 miles)

Day 6: Saltburn to Staithes  (9 miles)

Day 7: Staithes to Whitby (11.5 miles)

Day 8: Whitby to Robin Hood’s Bay (7 miles)

Day 9: Robin Hood’s Bay to Scarborough (15 miles)

Day 10 Scarborough to Filey (10 miles)


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

Official Cleveland Way website from the National Park Authority
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 ,ajor 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.

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