The Cleveland Way Guided Trail

We leave the delightful market town of Helmsley, passing the ruins of Rievaulx Abbey, set within the beautiful backdrop of the wooded Ryedale. Walking through the woodlands of Nettledale, we reach the small village of Cold Kirby then pass Hambleton Down, once the site of a major racecourse. Arriving at Sutton Bank we can admire the spectacular view over the Vale of York. We continue along the limestone edge of the Hambleton Hills, catching a glimpse below of Gormire Lake, one of only three natural lakes in Yorkshire. We then follow the historic Hambleton Drove Road, used since prehistoric times but especially during 18th and 19th centuries when Scottish cattlemen drove their herds down to market towns in England. We descend from the moor past the reservoir at Oakdale towards the attractive village of Osmotherley.

19½ miles (31.5km) with 2,450 feet (740m) of ascent.

Shortly after leaving Osmotherley, we join the route of the Lyke Wake Walk, which runs for 42 miles east to the coast at Ravenscar. Our rollercoaster path follows the northern escarpment of the North York Moors National Park, with outstanding views both north across the Vale of York and south and east into the moors. We will see signs of alum, jet and ironstone mining, reminders of the industrial past. We visit the massive sandstone blocks known as the Wainstones, before crossing the road at Hasty Bank to ascend Urra Moor to Round Hill, at 1,489 feet (454m) the highest point on the moor. Beside the trail we look out for moorland stone markers - the handstone marked an ancient route between Stokesley and Kirkbymoorside. The remotest point of the entire Cleveland Way is at Bloworth Crossing, once part of a busy mineral line bringing ironstone out of Rosedale to serve the developing industries of Teesside. Here we leave the Lyke Wake Walk, heading north again to drop down into Kildale.

20½ miles (33km) with 3,600 feet (1,100m) of ascent.

Leaving Kildale we cross the Esk Valley Railway, one of the few surviving "country" lines. We ascend Easby Moor to Captain Cook’s Monument, an impressive obelisk erected in 1827. From here the iconic Roseberry Topping comes into sight - the reward for reaching its 1,050 feet (320m) summit are outstanding views on all sides. Heading east we reach Highcliff Nab and continue through Guisborough Woods to leave the moors at Slapewath, passing through Skelton and a delightful wooded valley to reach the coast at Saltburn, a Victorian resort with a long stretch of sandy beach. We then rise quickly onto the cliff top, passing the remains of a Roman Signal Station on Hunt Cliff and a number of industrial sculptures before descending to Skinningrove.

18 miles (28.5km), with 2,250 feet (680m) of ascent; with Roseberry Topping option, 19 miles (30.5km) with 2,700 feet (820m) of ascent.

Beyond Skinningrove we ascend to the dramatic cliffs of Boulby, the highest on the Eastern coast of England at 666 feet (203m). Once more we pass evidence of alum workings before reaching Boulby Potash mine, the deepest in Europe. We continue to Staithes, with its picturesque harbour, narrow alleyways and cluster of red roofed houses. Another stretch of cliff path brings us to Runswick Bay where we can walk along the beach before going up onto the cliffs once more. Passing Kettleness, we are reminded of the ever-present nature of coastal erosion - the original village slipped into the sea in 1829. Our journey continues along the old railway line to Sandsend where we may be able to walk along the beach to Whitby.

18 miles (29 km) with 2,800 feet (860m) of ascent.

We leave Whitby by ascending the 199 steps to St Mary’s church, where the classic outline of Whitby Abbey comes into view. A pleasant walk along the cliff top brings us to Robin Hoods Bay, which marks the end of the Coast to Coast walk. The shore here is rich in fossils, the cliffs interrupted at Boggle Hole and Stoupe Beck. From here we ascend gently, passing through the extensive former alum works, considered one of the earliest sites of chemical industry. At Ravenscar we can learn about the “Town that never was”. From Ravenscar the trail continues along more wooded cliffs, dropping into the delightful wooded bay of Hayburn Wyke. We continue to Cloughton Wyke.

18 miles (29km) with 2,650 feet (800m) ascent.

The cliffs beyond Cloughton Wyke are lower, and soon Scarborough Castle comes into view. We continue towards this busy seaside resort, where there’ll be time for refreshments as we pass through the largest town on our route. As we leave Scarborough, we will see the former location of the Holbeck Hall Hotel, which famously slipped into the sea in 1994. Some of the bungalows at Knipe Point 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 and fitting end to our journey.

15½ miles (25 km) with 1,700 feet (520m) ascent.

Enjoy a leisurely breakfast before making your way home.