Cleveland Way: The Moorland Highlights

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.

Easy to 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: The North York Moors are rolling, sometimes remote, and up to 300m/1000ft high .

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, but these are usually well maintained.

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: The nearest train stations are Malton or Thirsk. You then travel by bus to Helmsley.
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 Saltburn by the Sea:
There is a Railway Station in Saltburn.

No recommended rest days available for this holiday