The Cleveland Way – Great Yorkshire Walks

The Cleveland way is a 110 mile walk, starting in the North Yorkshire Market town of Helmsley and finishing on the coast at Filey Brigg. It was opened in 1969 and is renowned for its stunning moorland and coastal scenery as it passes through the best of the North Yorkshire Moors National Park.

Cleveland Way
The Cleveland Way route. Source: sherpavan.c

There are many landmarks and points of interest along the way, so sit back and enjoy the journey!


Stage 1 – Helmsley to Sutton Bank – 10 miles (16km)

View from Sutton Bank. Photo credit, Paulie E, Geograph, Creative Commons
View from Sutton Bank. Photo credit, Paulie E, Geograph, Creative Commons

The traditional start of the Cleveland Way is at the Market Cross in the centre of Helmsley. Walk down the side of the Royal Oak Pub onto Castlegate and turn right. Turn left at the Feversham Arms Hotel, following the sign saying “Footpath to Rievaulx.” Proceed into the car park, where you are greeted with a sculpture containing an engraved acorn and depictions of the different places along the Cleveland Way. This was done by Whitby artist, Vivienne Mousdell and marks the walk’s official starting point.

Helmsley’s imposing castle, which even in ruined form still dominates the market town as it has done for over 900 years. Nowadays it is owned by English Heritage, but like many structures of its kind had a colourful history. It was besieged during the Civil War in 1644 and was eventually taken by the Parliamentarians, who slighted the castle, destroying much of its original structure, except for the adjoining mansion house. After the war it fell into the hands of banker and politician, Charles Duncombe and then his brother-in-law, Thomas Brown, who changed his name to that of his wife’s. Thomas saw little use for an old medieval castle and decided instead to build a country house nearby with adjoining parkland and named it Duncombe Park in 1713. The castle was left to decay until more recently, when it came under the care of English Heritage. The walk goes directly through the Duncombe Park estate, which is home to the International Centre for Birds of Prey, housing 60 species of eagles, owls and hawks.

Duncombe Park in Helmsley. Photo credit J E Hall, Geograph, Creative Commons
Duncombe Park in Helmsley. Photo credit J E Hall, Geograph, Creative Common

As the walk passes the northern edge of Duncombe Park, it passes through the site a deserted Medieval village called Griff, which is said to have been deserted around the year 1069, during the ‘harrying of the North,’ when the Normans laid villages to waste and burnt crops to maintain order. Local historians, including the owner of nearby Griff Farm have discovered evidence of earthworks dating back nearly 1000 years.

The village of Rievaulx is very much still here, along with its famous ruined abbey, which was founded by Cistercian monks in 1132. As with most abbeys it succumbed to Henry VIII’s forces during the Dissolution of monasteries in 1538. The ruins are slightly off the Cleveland Way, but if you wish to take a detour there is a well marked footpath to the abbey at Rievaulx Bridge.

The path winds through Rievaulx Woods, to the village of Cold Kirby. The 1841 St Michael’s church replaced an older one, which had a much darker history. A former priest at the church, James Tankersley, who was a monk at nearby Byland Abbey had a concubine in the village, which caused much scandal amongst his parishioners. After his death, the priest is said to have haunted the village, terrifying its inhabitants as he went, including one incident when he is alleged to have blown out the eye of his concubine. As a consequence the villagers dug up his grave in the churchyard and threw his coffin into the nearby Gormire Lake, which was said to be bottomless and surrounded by a dark, haunted wood.

The modern day St Michael's church at Cold Kirby. Source: geograph
The modern day St Michael’s church at Cold Kirby. Source: Geograph Photo credit, Scott Robinson

Here, you may if you wish take another detour to visit the White Horse at Kilburn. This is the largest chalk figure in the country at 314ft long and 228ft high and was created in 1857 by businessman, Thomas Taylor, plus teachers and pupils from the village school. It dominates the hillsides around Thirsk and on a clear day can be seen for many miles around. During the Second World War it had to be covered over to stop it becoming an aid to German bomber’s navigation. The horse is nowadays frequently re-covered with chalk from the Yorkshire Wolds to maintain its whiteness on the hill.

Stage 2 – Sutton Bank to Osmotherley – 11.5 miles (18.5km)

If you chose to visit the White horse at Kilburn, then you should double back on yourself to get back to Sutton Bank and start stage 2 of the walk. On the way back you are rewarded by passing the largest Iron Age hill fort in Northern England at Roulston Scar. Historians have revealed a massive 60 acre site with 1.3 miles of ramparts dating back to around 4000BC. Its position, overlooking miles of fields over the Vale of York suggest that not only was it used for defensive purposes, but also a statement of local power.

Along the path, leaving Sutton Bank is the aforementioned (and haunted) Gormire Lake, which is visible from the Cleveland Way as it leaves Sutton Bank. This is a glacial ox bow lake and was created around 20,000 years ago. In between lies the Yorkshire Wildlife Trust owned Garbutt Wood nature reserve, along with the impressive Whitestone Cliff. This is ancient woodland, said to date back to Tudor Times and is home to several species of plants, such as Ragged Robin, Common spotted orchids and Lady’s Bedstraw.

The mysterious Gormire Lake near Sutton Bank, Photo credit, Scott Rimmer, Wikimedia, Creative Commons
The mysterious Gormire Lake near Sutton Bank, Photo credit, Scott Rimmer, Wikimedia, Creative Commons

The path continues northwards through the Hambleton Hills. Eventually you will come across the remains of an ancient Iron Age Hill fort and settlement at Boltby Scar hill fort. Excavations at the site have uncovered the remains of trenches and ramparts dating back to the late Bronze/early Iron Age times. A barrow was uncovered with rings of golden hair attached to the bottom.

This path northwards is the site of the old Hambleton drove roads where Scottish traders would herd their animals down to markets in York and Thirsk.  Proceeding northwards and past the delightfully named “Hell Hole Wood” the path takes you to paradise. Well you are in Yorkshire aren’t you! In this part, everything seems to be named “paradise”, farms, roads, woods, everything.

The path takes you across Great Arden Moor and Black Hambleton Moor. The height has increased to around 1,300 feet above sea level and on a clear day in a northerly direction, the port of Teesside can be seen.

A good landmark amongst this expanse of moorland is Square Corner, which also has a car park. The Cleveland Way passes Oak Dale reservoir, before ending up in the village of Osmotherley. This is a sizable village with good facilities.

Stage 3 – Osmotherley to Clay Bank 11 miles (18km)

Directly to the north of Osmotherley and lying near the Cleveland Way is Mount Grace Priory. It may be worth taking a short detour if you wish to see this landmark. This is one of the best preserved ruins of a Carthusian monastery, which dates back to the 14th Century and is one of only ten of its kind left in the country. The Carthusian order of monks were notoriously silent and reclusive sect, which meant spending their days in silence and prayer; while socialising at night, on Sundays and during feast days. This area is known for its high stoat population, so look out for them running across the path as you walk.

Mount Grace Priory was once a place of silence and prayer
Mount Grace Priory was once a place of silence and prayer. Source: flickr

Just past here the Cleveland Way joins with other routes, such as the Coast to Coast and the Lyke Wake Walk, which originally was a 40 mile path, where grieving locals would carry the coffins of their deceased relatives to be buried at sea.

The beauty of the open moorland soon reveals itself, as the path takes you over five of them named Scarth Wood Moor, Live Moor, Cringle Moor, Cold Moor and Hasty Bank. On the latter you will see the Wainstones, which is a distinctive group of rocks which bear cup and ring engravings dating back to the Bronze Age. It is thought these stones were significant in prehistoric times. A view of what is to come; Roseberry Topping should also now be prominent on the horizon. Clay Bank is actually a B Road which crosses the footpath. Heading slightly north of here are two conveniently placed car parks if you wish to park there for next time.

The Wainstones
The Wainstones

Stage 4 – Clay Bank to Kildale (9.3 miles (15km)

Bloworth Crossing is a beautiful point on the trail and  next in your sights as you leave Clay Bank. This was once the site of an old mineral railway, which linked the villages of Ingleby Greenhow and Rosedale to serve the growing demand for metals on industrial Teesside. The crossing was an important intersection as it trundled south eastwards. This has now long gone along with the mineral industry in these parts. The nearby Urra Moor just to the South is the recognised highest point in the North Yorkshire Moors at 1,500 feet.

Urra Moor is the highest and remotest part of the Cleveland Way.
Urra Moor is the highest and remotest part of the Cleveland Way. Source:

You are now deep in the Cleveland Hills and about to head in a North Easterly direction towards the Southern edge of Middlesbrough and Guisborough.  The path turns sharply north at the old mineral crossing. Along this path you will find one of many carved stones, which were built to direct travellers across the moorland. This one dates back to 1757 and has a hollowed out head where travellers would put coins in for those who were in more desperate need out on the bleak landscape; something which is still in practice to this day.

In the distance the familiar shape of Roseberry Topping and the Captain Cook monument should still be in view as you approach the village of Kildale. This is a pleasant village, whose boundaries have never changed in 900 years. The site of its current 1868 built church of St Cuthbert is said to date back to Viking Times and was an important landmark.

Stage 5 – Kildale to Saltburn 14.75 miles (24km)

Leaving the village of Kildale, all routes point to the Captain Cook monument, which lies just one and a half miles away from the village. This obelisk on top of Easby Moor was built in 1827 in commemoration to the great explorer and cartographer. It overlooks the village of Great Ayton and provides great view of the surrounding area.

The Great Ayton Moor enclosure are the earthworks of several huts dating back to around 100-300BC. Look up and the imposing Roseberry topping is before you. Although the Cleveland Way does not pass directly over this local landmark, it is possible to detour off to climb it if you wish.

Roseberry topping is 1,049ft (320m) tall and has a distinctive half cone shape with jagged cliff at its summit. The strange half coned sandstone topping protects the underlying clay from the Yorkshire climate of wind, rain and snow. Before 1912, Roseberry Topping had a “sugarloaf” look to its summit, but due to a geographical fault of the effects of local mine works caused the hill to collapse to its current shape. In 1826 a hoard of Bronze Age axes and other implements were discovered and are now displayed (for some reason) at a museum in Sheffield.

Near Roseberry Topping the Cleveland Way lurches east, heading straight towards the sea. It skirts just to the south of Guisborough, which can be seen from Highcliff Nab on the route. This is a market town of 7500 people and believed to have Roman origins. The Guisborough Roman cavalry helmet was found nearby in 1864 and is on display at the British Museum.

The ruins of Guisbrough priory
The ruins of Guisbrough priory Source:

The Cleveland Way proceeds through Guisborough woods to the neighbouring town of Skelton in Cleveland to Saltburn by the sea. This Victorian seaside resort was one of the first of its kind and catered for the area’s working classes as a place for a holiday. Stretching further back, Saltburn was notorious for its smugglers. The town’s tiny houses and a more ready acceptance of this form of thievery meant that this industry thrived in places such as Saltburn. In some of the town’s older houses secret rooms can still be found, which were used to hide smugglers and their goods from enforcement officers who were chasing them for non payment of tax. Whole communities down this coastline, stretching from Saltburn to Scarborough became known as notorious smuggling hotspots. The Cleveland Way will take you right down this coastline as we perhaps enter the most fun part of the walk next to the sea.

Stage 6 – Saltburn to Sandsend 17.5 miles (28km)

Saltburn is the first coastal place on the Cleveland Way if you start at Helmsley.
Saltburn is the first coastal place on the Cleveland Way if you start at Helmsley. Source:

So, here you are on the great Yorkshire Coast. The rest of the Cleveland Way takes you through some of the finest coastal scenery in the country. Saltburn to Sandsend is a particularly lovely cliff top walk. Proceeding southwards from the Victorian seaside resort you walk past expanses of high cliffs, including Hunt Cliff and the wonderfully named, “Bird flight goit.” The track leads to Skinningrove, a friendly fishing and ex-mining village. In 2003 a very rare oarfish was caught here by a local fisherman. Past this village lies the highest cliff in on the East Coast at Boulby. It stands 203m tall and towers over the landscape and surrounding sea. Nearby is Boulby potash mine, which is the deepest in Europe.

Boulby Cliff is the highest on the East Coast
Boulby Cliff is the highest on the East Coast. Source:

Proceeding onwards and you arrive in Staithes, which is a quintessential north east coast fishing village, with lots of narrow streets and sea views. In its day, Staithes was one of the largest fishing ports on the North east coast and a hub of mining activity, especially in jet, potash and iron. It has a heritage centre, telling the history and stories of the coast, plus plenty of information on Captain Cook, who grew up near here.

The coast south of Staithes, where the Cleveland Way now takes us is known to scientists as the “dinosaur coast.” Along this stretch at places such as Port Mulgrave, many ancient fossils have been discovered, some of which date back to the Jurrassic era (150-200m years ago), when the area was covered by a huge sea. Fossils of ammonites, reptiles and larger sea creatures, which would have swum in this huge ocean millions of years ago, have been commonly found here, along with dinosaur bones and footprints.

After miles of cliffs, fossils and coastline comes Runswick Bay, arguably the most picturesque and romantic feature on the East Coast. Stop a while, take in the view. Fantastic! Along with the obvious there is plenty to explore in this tiny village, including the 19th Century Chapel, which was built in 1829 by the hard-working women of the village, along with its spring.

The magnificent Runswick Bay
The magnificent Runswick Bay Source:

Neighbouring Kettleness is the remains of a once larger village which was swept into the sea in 1829. Luckily at the time the residents were pre-warned and managed to evacuate before they watched their village fall down the cliffs. The Cleveland Way follows the track of the old Middlesbrough to Whitby line, which once ran through here before closing down in the late 1950s.

Just a couple of mile south of Kettleness is the larger entity of Sandsend. As the name may suggest one of the best parts of this place is its very sandy beach. It is a holiday resort in itself and seen as a slightly quieter alternative to nearby Whitby.

Sandsend beach is a distinctive feature on the coast.
Sandsend beach is a distinctive feature on the coast. Source:

Stage 7 – Sandsend to Robin Hood’s Bay 10 miles (16.3km)

The first place on the agenda, leaving Sandsend on the Cleveland Way is Whitby. There isn’t much more that needs to be said about one of the most popular coastal destinations in Yorkshire. Its abbey stands proudly on top of the cliff, along with a wonderful harbour and river which famously divides the town in two. Whitby also has all the trappings of a modern seaside town with sandy beach, amusement arcades plus some of the best fish and chips in the county. The Cleveland Way passes its large beach, its famous pier and over the bridge, before escaping up the 199 steps to the Abbey and leaving the town southwards along the East cliff. Whitby is a north-facing port, so you are in fact heading in an easterly direction at this point in the walk.

Whitby little more needs to be said.
The Cleveland Way passes directly through Whitby. Source: tumblr

The way follows yet more expanses of cliffs. On the way you will come across Maw Wyke Hole, which is where the Coast to Coast joins the Cleveland way to its own ending point at Robin Hood’s Bay. If you come across a fellow walker who is trying desperately to reach the end of the Coast to Coast, please help them complete the final part of the walk with you and buy them a well earned pint in Robin Hood’s Bay.

It is unlikely that the famous legendary figure, Robin Hood, ever visited the bay and after all he was based many miles away around Nottingham. Local legend has it though that he did encounter French pirates here and managed to defeat them, before stealing their bounties and distributing them to the poor of the village. Like Saltburn, this bay was notorious for smugglers. Battles between these “criminals” and excise men were commonplace in the bay throughout 17th and 18th Centuries.

The village has many local facilities for you to stop and refresh yourselves before heading down to Scarborough.

The iconic Robin Hood's Bay.
The iconic Robin Hood’s Bay. Source:

Stage 8 – Robin Hood’s Bay to Scarborough 12 miles (19.3km)

There are two words on your lips as you leave Robin Hood’s Bay for the next section of the walkBoggle Hole. Despite its unusual name it is a site of special scientific interest due to the large amount of fossils on it shore. If you wish to stop and hunt for fossils here please be fully aware of local weather conditions and tide times, especially as the most fossils are to be found during the winter months.

The next point of interest along the Cleveland Way is Ravenscar. In the Victorian Times a consortium of gentlemen had the bright idea of building their own seaside resort here. Lavish plans for hotels, chalets, gardens and attractions were submitted and approved. A sewage system was put in place and a railway built to ferry tourists from other parts of the North to enjoy the delights of Ravenscar. Unfortunately these plans only partly came into fruition, due to several factors, including the cliffs being too steep to build a railway line, the inclement weather off the sea and the fact that Scarborough and Whitby were probably much better. The remains of this half built resort can still be seen to this day, including road layouts and gardens. The company behind it went bust in 1913 and it was left to mercy of the Yorkshire climate. Ravenscar Hall, nowadays the big hotel on the cliff was built in 1774 and was owned by the Willis family. The head of the house was also King George III’s doctor and it is said that the monarch spent some time in Ravenscar during his bouts of madness. It became a hotel in 1895, originally as part of the holiday resort project, but unlike this has continued successfully ever since.

The remains of Ravenscar holiday resort makes a fascinating landmark on the Cleveland Way,
The remains of Ravenscar holiday resort makes a fascinating landmark on the Cleveland Way. Source:

Heading southwards towards Scarborough you pass Beast Cliff, which is once again a site of special scientific interest and one of the best examples of a vegetated sea cliff on the East Coast. In days gone by animals would be hoisted down by ropes to graze on this inaccessible plateau.

Another interesting geographical feature along this coastline is “Herbert Hole,” a rock pavement near to Hayburn Wyke. This area is also a nature reserve owned by The National Trust. Animals such as Roe Deer, badgers and foxes are common here, along with summer birds such as Redstart, Blackcap and resident woodpeckers.

Herbert Hole is an interesting geographical feature
Herbert Hole is an interesting geographical feature.

As you head closer to Scarborough and its castle, which should come into view as a misty blob in the distance, the coastline is littered with distinguished features. One of which is Long Nab, a bay and another site of special interest for birdwatchers. A sea watching hide has been constructed here to study the behaviour of terns, shearwaters and divers, which can be viewed over the sea and on the nearby cliffs. Scalby Ness is another magnet for fossil hunters. Before you know it you will be entering Scarborough’s North Bay and Castle area, which now looms large.

The familiar Scarborough sea front.
The familiar Scarborough sea front. Source: trip advisor

Stop a while in Scarborough, enjoy some fish and chips and view its famous castle and bay.

Stage 9 – Scarborough to Filey Brigg 10.5 miles (16.7km)

The Cleveland Way passes right along Scarborough sea front, past the harbour and South beach. Heading southwards, past the black rocks, you will encounter the popular holiday destination that is Cayton Bay. It is geographically significant too. The rocks around here were formed 150 million years ago during the Jurassic Period and like much of this coastline is a haven for fossil hunters. It is also noted for its award winning beach and sweeping landscape.

Holiday destination- Cayton Bay
Holiday destination- Cayton Bay Source:

In Cayton Bay lies the Calf Allen Rocks, which is place where you can view seals depending on the time of year. Further on, Gristhorpe Cliffs is where a Bronze Age skeleton was found in 1834 and now an exhibit at the Scarborough Rotunda museum. The man in question was a chieftain of the local tribe in around 1,500BC.

As the Cleveland Way proceeds southwards towards Filey the cliffs become slightly lower, but this is not to say that the views are still fantastic. This stretch of coastline, containing little inlets, coves and bays runs for several miles, until you hit Filey Brigg and the end of the Cleveland Way, which becomes the Wolds Way. Well done for reaching the end of this magnificent Yorkshire walk of moorland and coast.

cleveland end of cleveland way
The end of the Cleveland Way at Filey Brigg Source: yorkshire