Cleveland Way Coastal Section Guided Trail Holiday

Check-in at the hotel is available from 16:00. If you are a member you can arrive at the house from 14:00. Enjoy a complimentary cream tea at 16:30 and meet other guests.

Leaving Filey, we pass the sculpture that marks both the start of our trail & also the start/end of the Wolds Way. Gentle walking along low cliffs eventually brings us to Cayton Bay with its popular surfing beach, the first of several fine beaches we will pass on our trail. An undulating path through woodland & along cliff tops brings us to Scarborough, Britain’s first seaside resort. We descend to sea level as we walk along the promenade of South Bay, passing the towering Grand Hotel, once the largest hotel in Europe. From South Bay we climb up onto the headland, with views up to the castle, to visit Anne Bronte’s grave. From there we descend to the quieter North Bay to finish our day. 

10 miles (16km) with 1,050 feet (320m) of ascent 

We leave Scarborough along the promenade of North Bay with its brightly coloured beach huts. At Scalby Mills a short climb up onto the cliffs brings pleasant walking with fine views up and down the coast. We descend into the woodland of Hayburn Wyke with a chance to see the waterfall that falls directly onto the beach. A steep climb out of the Wyke leads to a path that ascends gently all the way to Ravenscar, the Town That Never Was. On the way we pass an old wartime radar station and at Beast Cliff we may be able to spot highland cattle grazing far below us on the undercliff. 

10 miles (16km) with 1,400 feet (430m) of ascent

Discover more about Larpool Hall and the local area for ideas on how to make the most of your free day.

From Ravenscar, perched high up on the cliff, we drop down to visit the remains of an old alum production site. From there we make our way to the old fishing & smuggling village of Robin Hood’s Bay with its winding passageways. We now climb up onto cliffs that stretch almost unbroken to our eventual destination of Saltburn. For the first few miles our path is shared with Alfred Wainwright’s Coast To Coast path, before continuing on the Cleveland Way, with wonderful views along the cliffs. After passing High Whitby lighthouse Whitby Abbey soon comes into view to show us the way into Whitby itself. We descend the 199 Church Stairs before a walk through the cobbled streets past several jet shops. 

11.5 miles (18.5km) with 1,400 feet (430m) of ascent

Leaving Whitby, we pass the Whalebone Arch and the statue commemorating Captain James Cook before a walk along the newly renovated promenade. We walk on to Sandsend before a disused railway line leads us to a steep, stepped climb up to the cliff tops once more. After passing the hamlet of Kettleness, we descend to the mysterious Hob Holes and cross the beach to the picturesque Runswick Bay. A further climb takes us back up again for a final walk to Port Mulgrave, an old ironstone port. 

12 miles (19.5km) with 1,200 feet (360m) of ascent 

Our final day starts with a short walk along the cliff tops to Staithes, another fishing village tucked into a narrow valley to protect it from the fierce North Sea. From sea level we climb up to the highest point on England’s east coast, the 666ft (200m) high Boulby Cliff with its panoramic views and abandoned alum works half way down the cliff. We descend once again to sea level to the old ironstone mining village of Skinningrove, before a final climb takes us past the Charm Bracelet sculpture, before a final descent to the elegant Victorian seaside resort of Saltburn-By-The-Sea with its pier, the only one on the Yorkshire coast. 

11.5 miles (18.5km) with 1,300 feet (400m) of ascent 

Enjoy a leisurely breakfast before making your way home.