Cleveland Way

Arrive in Helmsley, a pleasant market town, and spend the evening at your first night’s accommodation.

The Cleveland Way begins in Helmsley. Your first days walk is fairly easy, across the beautiful landscape of the Rye Valley where a short detour takes in the ruins of splendid Rievaulx Abbey.

The route then climbs onto the flat plateau of the Tabular Hills to Hambleton Hill, before it descends into the hamlet of Sutton Bank with views over the distant Pennines. Allow time to visit the White Horse of Kilburn, a limestone horse carved into the hillside on the way. Due to lack of accommodation in Sutton Bank, transport back to Helmsley is provided.

From Sutton Bank the walk traces the western edge of the North York Moors National Park and the views are truly breathtaking. Follow part of the Hambleton Drove Road for a few miles; an ancient upland thoroughfare, before the climb up to Hambledon End; at 1309 feet, the high point of the day. There are great views from the ridge before the route descends to the charming village of Osmotherley with its quaint shops, cafes and pubs.

This section of the Cleveland Way is remarkably hilly, a roller-coaster of a walk up and down the Cleveland Hills and the most strenuous section of the route. On a clear day this is a very scenic and beautiful stretch providing stunning views over the coastal plain to the North and across the bleak moors to the South. Your accommodation tonight is in the village of Great Broughton located 2 miles off the trail.

This is the most remote section and across the highest part of the North York Moors. Climb over Urra Moor to the summit of Round Hill, at 1489 feet the highest point of the route and enjoy sweeping views. In calm, clear weather this is one of the most memorable parts of the route, however on a bad day the moors can be windswept and inhospitable.

From Tidy Brown Hill the route descends through Battersby Moor into the village of Kildale. Continue on from Kildale and the Cleveland Way now enters Captain Cook country. The route climbs up Easby Moor to visit Captain Cook’s Monument, born nearby in 1728.

A few miles further on from the Captain Cook’s Memorial, the route takes a steep climb up the eroded sand stone stump of Roseberry Topping, the ‘Yorkshire Matterhorn’ – although only 1000ft high, this distinctive conical hill is prominent in the landscape.

The bustling town of Guisborough can be seen, but the Way passes high above it over Guisborough Moor and onto the gentler farmland leading to the coast and the Victorian seaside resort of Saltburn.

From Saltburn the Cleveland Way enjoys its first day along the coast, taking in splendid cliffs and coves. Head up Hunt Cliff and along a section of dramatic cliffs. There are several stiff climbs on this section of the walk and you will be climbing up around 1000 feet – the second cliff at Boulby is the highest on the East coast of England. In between the hills however the route descends to sea level losing all the height you have gained!

From Boulby descend to the charming and colourful harbour village of Staithes. Visit the excellent Captain Cook and Staithes Heritage Centre. The cliff coast continues to Runswick Bay, another delightful little village situated on a steep slope facing the bay.

From Runswick Bay follow the dramatic coast path to Sandsend before enjoying an easy stroll to Whitby; probably the most special town along the route with its Old Town, fine harbour and fossil filled cliffs. Most walkers want some time to explore the narrow streets and bustling harbour-side of this old whaling town.

Whitby and Robin Hood’s Bay are separated by an easy cliff top walk. Arrive in Robin Hood’s Bay, a delightful heap of houses clinging to steep slopes.

Leave Robin Hood’s Bay and from here to Scarborough the scenery changes continually, with Flyingdales Moor to the west and the North Sea to the east. The route follows a roller-coaster path along the cliffs and this section is a lovely peaceful walk. Ahead lies the busy seaside town of Scarborough with its grand beaches and traditional seaside entertainment!

Away from the bustle of Scarborough the final leg of your Cleveland Way walk takes you out along the esplanade above South Bay where you could visit the old castle and spa complex and enjoy some of the town’s history and heritage before you leave.

The view of continuous coastal cliffs continues as you enjoy easy walking on the cliff paths until your final destination, the small fishing town of Filey.

After breakfast, you will start your journey home after a wonderful walking holiday on the Cleveland Way.