Cleveland Way

Helmsley to Sutton Bank – 10 miles (16 Km)

This section is a good introduction to the Cleveland Way. The walking is not too strenuous as it climbs out of the Rye Valley to reach the Hambleton Hills escarpment at Sutton Bank.

There cannot be a finer start to a National Trail than the delightful market town of Helmsley, centred around a historic market square. Helmsley Castle is clearly visible as you start to climb out of the town. Look out for the Start Feature, sculpted by the Whitby artist Vivienne Mousdell which shows the characteristic National Trail acorn as well as the names and profiles of places along the “Way”.

Soon you pass the fascinating ruins of Rievaulx Abbey, set within the beautiful backdrop of the wooded Rye Valley for 800 years.

Heading west you walk through the managed woods and past the ponds at Nettledale, then climb gradually to reach the small village of Cold Kirby. There are no facilities here so journey on towards Sutton Bank passing the famous site of the Hambleton Down racecourse. It is hard now to believe that this was once one of the top racecourses in the country. The tradition continues however as you will pass the Hambleton racing stables which are based here.

The final part of this section takes you through to the dramatic escarpment of Sutton Bank – the western gateway to the North York Moors National Park. The author James Herriot lived just a few miles from here and once described this view over the Vale of York as “the finest in England”.

At the southern end of Sutton Bank is the enormous figure of the White Horse of Kilburn. This is not an ancient figure as are its southern relatives, but was dug out by local schoolmaster John Hodgson and 30 volunteers in 1857.

Having looked out for gliders, who also enjoy the benefits of this escarpment, your visit will be completed with a visit to the award winning Sutton Bank National Park Centre where there is a host of information as well as guides, refreshments and toilet facilities.

Sutton Bank to Osmotherley – 11.5 miles (18.5 Km)

This section of the Cleveland Way takes you along the limestone Hambleton Hills of the North York Moors National Park. You will be following in part an ancient route followed by drovers and travellers for centuries.

Cyclists and horse riders can enjoy a significant part of this section, joining the route just north of Sutton Bank and leaving it on the Drove Road east of Osmotherley. Cycle Hire and local route information is available at Sutton Bank

Start your journey with a visit to the award winning Sutton Bank National Park Centre. There is no better way of discovering all about the North York Moors National Park. Heading out on the Cleveland Way you will soon spot Gormire Lake. This is one of only three natural lakes in the whole of Yorkshire.

As you journey north along the escarpment you will join the historic Hambleton Drove Road. This route has been used since prehistoric times but is mainly remembered for its time in the 18th and 19th centuries when Scottish cattlemen drove their herds down to market towns in England.

Descend from the Drove Road and head towards the former reservoir at Oakdale and you will come across the first signs of path restoration. This work was needed to combat the devastating effects of path erosion. The section near to the reservoir won the British Upland Footpath Trust award for path restoration in 1996 because of the sympathetic way in which the work had been carried out.

Soon you will reach Osmotherley, a most attractive village in which to end your visit. It has several pubs, a café and nearby hostel and camping provision.

Osmotherley to Clay Bank – 11 miles (18 Km)

This length of the Cleveland Way takes in the magnificent Cleveland Hills. The northern escarpment of the North York Moors National Park offers outstanding views both north across to Teesside and south and east into the moors and dales of the Park.

Heading north out of Osmotherley the route runs within half a mile of Mount Grace Priory. Managed by English Heritage and the National Trust, this former Carthusian Monastery is worth a detour.

Now the dramatic moorland landscape of the Cleveland Way really starts to take hold. This section crosses over 5 moors, Scarth Wood Moor, Live Moor, Cringle Moor, Cold Moor and Hasty Bank. All of these have undergone major path restoration.

Along the way you will see signs of alum, jet and ironstone mining. These are reminders that the North York Moors has an industrial past, supplying raw materials to Teesside during the industrial revolution.

The  Lord Stones Cafe at Carlton Bank provides an excellent refreshment point along this length. Camping and camping pods are also available here. Beyond this you will come across the massive sandstone blocks which form the Wainstones. Rock climbers will often be encountered here. Continue along Hasty Bank with its stunning views into the North York Moors National Park and beyond.

Clay Bank to Kildale – 9.3 miles (15 Km)

This section continues the upland moorland theme – with a chance to visit the highest point on the North York Moors. Signs of old industry are never far away as part of the route joins the old railway line near Blowarth Crossing. 

Mountain bikers and horseriders can also enjoy this full length between Clay Bank and Kildale.

Heading up onto Urra Moor you will pass the highest point in the North York Moors at 454 metres (1489 feet). Look out for the moorland stone markers on this length. One has a carving of a hand, the other a face. Stone markers and crosses are found throughout the North York Moors. The handstone here marked a route between Stokesley and Kirkbymoorside.

The remotest point of the entire Cleveland Way is at Blowarth crossing beyond Urra Moor. Incredibly this was once a railway crossing bringing ironstone out of Rosedale to serve the developing industries of Teesside and Durham.

Head north again from here to drop down to the small village of Kildale, where there is accommodation, toilets (at the station) and usefully, rail connections to Whitby and Middlesbrough.

Kildale to Saltburn – 14.75 miles (24 Km)

On this section of the Cleveland Way you enter Captain Cook Country and will come across several reminders of the famous explorer who grew up in Great Ayton.

Heading north out of Kildale you will cross the Esk Valley rail line. This is one of the few surviving “country” lines.

Before long the views open out on Easby Moor. Unmissable here is Captain Cook’s Monument, a large obelisk erected to his memory in 1827. From here Roseberry Topping comes into sight. This is one of the North York Moors most famous landmarks, standing isolated from the rest of the Cleveland Hills. Its shape gives it its nickname as “Yorkshire’s Matterhorn” and the reward for reaching its 320m (1050 feet) summit is a panorama of outstanding views.

Nearby Great Ayton is worth a detour, with the informative Captain Cook Schoolroom Museum.

Heading east you enter Guisborough Woods. The longest stretch of forestry on the Cleveland Way, it offers glimpses of the plain below with excellent views over Guisborough from Highcliff Nab. Just off the Cleveland Way at the foot of the woods lies the Guisborough Branch Walkway and Visitor Centre. The Fox and Hounds Pub/ Chase Eatery at Slapewath offers sustenance before the final stretch through Skelton and the delightful Saltburn Woods, before reaching the sea at Saltburn.

Saltburn to Sandsend – 17.5 miles (28 Km)

This section is a great introduction to the North Yorkshire coastline. You will soon understand why most of it falls within the designations of both National Park and Heritage Coast.

Saltburn is worth exploring. It rose in popularity with the Victorians seeking seaside resorts. Its fine pier is frequently adorned by Saltburn “Yarnbombers” and the town has become especially popular as a surfing destination. The Cleveland Way heads south out of Saltburn rising quickly onto the cliff top. You may be surprised to come across several art features along this stretch. The most distinctive of these metal sculptures is the Charm Bracelet  – a circle with ten metal objects representative of the area hanging and clanking from it in the breeze!

Beyond Skinningrove you will climb up to Boulby Cliff. This is the highest cliff on the eastern coast of England at 203 metres (666 feet). Another record is set nearby – you will see the Boulby Potash mine which is the deepest mine in Europe.

Beyond Boulby you drop down to Staithes, a most picturesque harbour village with narrow alleyways and a cluster of houses. There are pubs and cafes to enjoy and accommodation should you wish to spend the night here.

Take in the sea air as you travel on to Sandsend and enjoy the beach at Runswick Bay before climbing the cliffs once more. The original village of Kettleness slipped into the sea in 1829, a reminder of the ever present nature of coastal erosion along the Cleveland Way. Your journey continues through to Sandsend where there is a wealth of tea shops and pubs.

Sandsend to Robin Hood’s Bay – 10 miles (16.3 Km)

This section covers some outstanding coastal scenery as well as visiting popular seaside resorts such as Whitby and Robin Hoods Bay.

Your journey from Sandsend soon reaches Whitby, a famous sea side town which prospered through the years from whaling, shipbuilding (Captain Cooks ships were built here) and the jet trade. Today tourism is one of the main industries. Whitby is also renowned as the setting for Bram Stokers “Dracula”.

Enjoy counting the 199 steps up to St Mary’s church – everyone else does! The classic outline of the ruins of Whitby Abbey, managed by English Heritage soon comes into view.

Follow the pleasant walk along the cliff top through to Robin Hoods Bay. Here the houses are clustered so closely together that they appear to be nesting on the cliff edge. Robin Hoods Bay is infamous for its role in the smuggling trade between 1700 and 1850. Pubs, cafes, B&Bs and toilet facilities are all available so that you can stop and enjoy the beauty of this village, which also marks the end of the Coast to Coast walk.

Robin Hoods Bay to Scarborough – 12 miles (19.3 Km)

This classic stretch of the trail heads up towards the distinctive heights of Ravenscar, so affording outstanding views across the landscape and sea.  You will encounter the hidden delights of Hayburn Wyke and its beach, before the historic seaside town of Scarborough comes into view.

Public transport on this length is excellent – with hourly buses available

Heading south once again is the gradual climb to Ravenscar, with the occasional sudden drops to sea level at Boggle Hole and Stoupe Beck. Approaching Ravenscar you pass through site of former Alum works, considered one of the first sites of the Worlds first chemical industry. It is worth calling in at the National Trust centre at Ravenscar to get local information and to learn about the “Town that never was”. Ravenscar has both toilet and refreshment facilities.

Heading south from Ravenscar the trail drops into the delightful wooded bay of Hayburn Wyke. This is a fantastic spot to stop by the waterfall and admire the stone pebble beach.  Nearby the Hayburn Wyke Inn is a great source for refreshments.

Journey on and soon Scarborough Castle comes into view. Keep heading on towards this busy seaside resort. On reaching Scarborough you can choose to take the open top bus around from North Bay to the Spa at South Bay or enjoy this exhilarating walk around its promenade from North Bay to South Bay.

Scarborough to Filey – 10.5 miles (16.7 Km)

This final length has some stunning cliff and coastal scenery to appreciate as you saunter through to the lovely old Victorian resort of Filey.

Regular public transport by rail or bus is available between the two towns.

Passing out of Scarborough you will see the former location of the Holbeck Hall Hotel. The hotel famously slipped into the sea in front of the British media in 1994.  In fact coastal slippage is a frequent reminder here, as you head past the bungalows at Knipe Point some of which have also been lost to the sea in recent years.

The walk passes above the beautiful expanse of Cayton Bay before you enjoy the last few miles through to the stunning geographical location of Filey Brigg, a birdwatchers paradise. This point marks the finish not only of the Cleveland way but also the Yorkshire Wolds Way another National Trail that follows the gentle rolling landscape of the Yorkshire Wolds between Hessle on the Humber and Filey.

Put your feet up and rest at the end feature at Filey Brigg which marks the completion of the 2 National Trails. After all you deserve it!