Cleveland Way

Helmsley to Osmotherley

The first section of the Cleveland Way provides an easy woodland walk across the beautiful landscape of the Rye Valley, passing the ruins of Helmsley Castle and later the medieval Rievaulx Abbey. These ruins are among the most beautiful in England and the dense wooded valley of the river Rye provides a magnificent setting. The walk then rises gently to the flat limestone plateaux of the Tabular Hills. It is also worth allowing time to visit the Kilburn White Horse, just before Sutton Bank.

From Sutton Bank the walk is relatively flat, following the western edge of the Hambleton Hills overlooking the Vale of York. The views from Sutton Bank are breathtaking. From High Paradise to Black Hambleton the route follows the old road used by the cattle men (drovers) in earlier centuries. After Black Hambleton you drop down to the idyllic setting of Oakdale’s reservoirs, en route to Osmotherley.

Osmotherley to Kildale

This is the most strenuous section of the trail, as the route follows the northern escarpment of the moors, broken by a series of valley’s cutting into the uplands between Huthwaite Green and Clay Bank Top. The views are stunning over the coastal plain to the North and across the bleak moorland and deep valleys to the South.

After Clay Bank Top a steep climb leads up to Round Hill, the highest point on the route, where tremendous views can be enjoyed. The route then descends gradually to Kildale which is studded with signs of the past – waymarkers, boundary stones and burial mounds.

Kildale to Saltburn-by-the-Sea

The first part of today’s walk is dominated by an ascent of Easby Moor, to Captain Cook’s Monument, and then the moorland ‘Matterhorn’, Roseberry Topping. Although only 1000ft (300m) high, this distinctive conical hill is prominent in the landscape. From the top the views are excellent. Gentler farmland, woodland and a riverside path lead onto the coast at Saltburn-by-the-Sea.

Saltburn-by-the-Sea to Robin Hood’s Bay

From here on the route hugs the coastline, through historic fishing villages, over high cliffs and along windswept beaches. From Saltburn the route heads up Hunt Cliff and along a section of dramatic cliffs to the highest point on the east of England at Rock Cliff. This route takes you down to sea level on three occasions and through the pretty villages of Staithes and Runswick, ending at the fishing village of Sandsend.

Dramatic coast paths lead onto Whitby, with its fine harbour, fossil filled cliffs and old town connections with Bram Stoker’s Dracula! A visit must be made to the imposing remains of Whitby Abbey high above the town.
Whitby and Robin Hood’s Bay are separated by an easy cliff top walk.

Robin Hood’s Bay to Filey

Between Robin Hood’s Bay and Scarborough the route encompasses ever-changing scenery, with the Flyingdales Moor to the west and the North Sea to the east. There are three steep descents and ascents along this path, where the sea interrupts the cliff top walk.

The arrival into the seaside town of Scarborough will provide you with another type of scenery, with its grand beaches, swish hotels and traditional seaside entertainment!

On leaving Scarborough, notice the vibrant colours from the South Cliff as you make your way to the final cliff top trail. The view of continuous coastal cliffs continues from Cayton Bay until your final destination, Filey.

Moderate

The route covers rolling countryside and moorlands, but not mountains. If you are a regular walker this route should be within your capability.

Terrain: A walk of two halves – the North York Moors are rolling, sometimes remote, and up to 300m/1000ft high . The coastal path follows the cliffs with frequent descents to coves and beaches.

What’s it like underfoot? On the whole the paths are well defined and maintained, but at times it can be rough underfoot with some muddy paths, so good footwear is essential.

How much up & down? There are climbs of up to 300m some of which can be quite steep, through the Moors section, and short, sometimes steep climbs from sea level along the coast.

Signposting: Generally good.

Navigation: Pretty straightforward, but you may encounter hill fog or low cloud on the North York Moors, so make sure you can navigate.

Good accommodation and friendly hosts are an essential part of any holiday. We understand this and go out of our way to find the best. We put a great deal of effort into hand picking our accommodation and matching it to individual customer requirements. As well as visiting the accommodation ourselves, we ask all our customers to complete a short evaluation on each night’s accommodation, which then gives us an insight into the day-to-day operation and lets us spot any potential issues before they become a problem.

We use a variety of accommodation. Over the course of your trip you might stay in a village inn, a bed and breakfast in a converted barn, a Victorian guest house, or on a working farm. In selecting the accommodation we look for helpful, friendly hosts with good quality, characterful accommodation close to the trail. Occasionally we may use a chain hotel.

We always try to arrange en suite accommodation, i.e. rooms with their own bathrooms for each night of your stay. However, in some of the more remote locations accommodation is limited and occasionally we may have to book rooms with shared bathrooms for one or two nights of your holiday, (especially if the booking is made at short notice), but we will always let you know if this is likely to be the case.

We are happy to book single rooms on our holidays but cannot normally book more than two for any one group. Single room bookings include a supplement.

Here are some examples of the accommodation we use on the Cleveland Way:

The Feathers Hotel, a 16th-century coaching inn in Helmsley, offers more than just a place to stay. Guests can enjoy cosy fires in winter, a spacious courtyard in summer, and exceptional seasonal menus showcasing the finest flavours of North Yorkshire and beyond, all in a warm and welcoming atmosphere. Visit their website

The Golden Lion in Osmotherley, set in the heart of the picturesque North York Moors National Park, is a historic inn with a warm, traditional charm. Popular with both locals and visitors, it offers classic pub fare, real ales, and fine wines. Comfortable, stylish rooms provide the perfect retreat after a day exploring the area’s stunning surroundings. Visit their website

The family-run Spa Hotel in Saltburn offers breathtaking panoramic views of Huntcliff, the North Sea, and the surrounding countryside. Guests can enjoy spacious, comfortable rooms, many with stunning sea views. For ultimate relaxation, the Amber Rooms provide soothing massages and revitalising facials, making it the perfect seaside retreat Visit their website

Wendy & Gareth offer you a warm & friendly welcome to The Forge Guest House in Filey. Their delightful property is perfectly situated in a quiet location with the wonderful golden beach, cliff top walks, cafes, restaurants & pubs, only a few minutes stroll away. Visit their website

General travel information on the Cleveland Way area will be in your holiday pack including train and bus timetables where available.

Detailed instructions on getting to your first night’s accommodation by car, or on foot from the nearest train or bus station, will also be included in the holiday pack on individual accommodation maps.

To view train times please visit trainline where you can also purchase tickets in advance. For information on bus timetables please visit traveline

If you require secure car parking whilst walking this route, we can usually arrange this in Helmsley. To return to your car we recommend using a taxi transfer as the journey by public transport is not very convenient and takes a long time.

Getting There:
By Air: The nearest International Airport is Leeds Bradford (LBA) You can then travel by train to Malton (journey time 55 mins approx) and then bus to Helmsley (16 miles). You can also fly to Newcastle (NCL) or Manchester (MAN) – from either of these airports you can take the train to Thirsk, and then bus to Helmsley.
By Public Transport: From York train station take a train to Malton (journey time 25 minutes) where you can take a bus (or taxi) to Helmsley 16 miles away.
By Road: Helmsley lies on the A170 (Thirsk to Scarborough Road) 14 miles east of Thirsk, and 13 miles west of Pickering. It is also at the end of B1257.

Returning from Filey:
Taxi: If you wish to return to Helmsley at the end of your walk, it is a difficult journey by public transport. We would be happy to arrange a taxi for your return journey.
Rail: Regular train services operate from Filey to London Kings Cross via Scarborough and York and North to Edinburgh on the East Coast mainline.

Robin Hood's Bay

This picturesque village is a hidden gem on the East Yorkshire coast consisting of a maze of tiny streets with individual shops, cafes and pubs. Robin Hood's Bay has a tradition of smuggling (during the late 18th century smuggling was rife on the Yorkshire coast) and there is reputed to be a network of subterranean passageways linking the houses. The rocks of Robin Hood’s Bay play host to a wealth of Jurassic history and fossilling is a wonderful activity for people of all ages along the huge, unspoilt beach. Likewise, the thrill of finding your first crab or starfish in a rock pool is equally as pleasurable.

Filey

A small, attractive seaside town with a long history of fishing, Filey has a magnificent beach with dramatic views of the long black finger of Filey Brigg in one direction and the chalk headland of Flamborough Head and Bempton Cliffs in the other.  It is well worth taking an extra day here to visit the RSPB Reserve at Bempton Cliffs. The Reserve is home to around 200,000 nesting birds including gannets, guillemots and kittiwakes during the breeding season.  Just a short distance further along the coast is the magnificent Flamborough Head, one of the best–preserved chalk headlands in Britain and home to the oldest complete surviving lighthouse in the UK.