12-day Cleveland Way Walking Holiday

Make your own way to Helmsley and settle into this attractive old market town. Visit the ruins of the castle keep with echoes of the English Civil War in 1644. There are nice pubs, cafes and shops to browse and visit.

After breakfast depart Helmsley on this easy section across the wooded Rye Valley, then ascend gently up to the Tabular Hills and onto the great viewpoint at Sutton Bank, with views to a Victorian chalk horse carved into the hillside. Enroute you can visit the famous 12th century Rievaulx Abbey.

Today is more or less level walking along the escarpment of the Hambleton Hills with views over the vale of York. The walk follows the ancient Hambleton Cattle Drovers Road to the old market and mining village of Osmotherley with the remodeled 15th century church with 12th century Scandinavian carvings.

After the warm-up of the last couple of days, hopefully you are ready to enjoy what most people would claim to be the hardest day of the route, as you are ascending and descending over a succession of moors to Clay Bank Top. The views in reasonable weather are extensive. The Coast-to-Coast shares this day and it is a roller coaster ride of a walk up and down beside the crags of Cringle Moor and the famous Wainstones. We come off the ridge at Clay Bank Top and you will get a transfer to your accommodation (included) from the car park at Clay Bank Top down the hill to Great Broughton.

*Overnight in Great Brougthon

Your host transfers you back to Clay Bank car park and then you start the day with a steep ascent up onto Urra Moor and the highest point of the journey at Round Hill (454m). You are now walking on exposed high moorland, following the line of the disused Ironstone railway line and drovers roads, with many ancient features, such as boundary stones, tumuli and cock pits before descending to cross the remote hamlet and railway station at Kildale. Ascend again, passing the Captain Cook memorial.

The walk continues through forests with a diversion to “Rosberry Topping” an outlying craggy hill. It is a steep climb, but the views on a clear day are outstanding. The trail follows more moorlands and then through the Guisborough woods and steeply down to Slapewath, an area of old mineral workings. Perhaps fortify yourself with a pint before continuing the last 7 km/ 4.5 miles to Saltburn-by-the-Sea; an old fishing village; come small Victorian seaside resort that was once famed for salt making and smuggling! The whole nature of the walk changes from here as you head off along the coast.

Walk along successive dramatic cliffs, past the highest point on the English east coast at “Rock Cliff” near Boulby. Highlight of the walk today is the beautiful little fishing village of Staithes. The fishing boats at the quay are called Cobles and they still set out to undertake this dangerous activity. Captain Cook served his apprenticeship in a shop on the seafront which has long ago, been stolen by the sea! The trail continues onto the red roofed attractive village of Runswick Bay, by the Jurassic shale cliffs, a fossil hunter’s paradise!

Quite a short day giving you the chance to have a good look round Whitby.

From Runswick, there is another section of cliffs before reaching Sandsend, from where you walk along above the beach into Whitby. This red-roofed town grew rich especially between 1750 and 1850 on fishing, whaling, mining and shipbuilding. Whitby is also famous for its Abbey ruins and for Count Dracula (there is a Dracula Trail in the town). We would recommend that of all the places on this route, you have a fish 'n' chips meal here!

The shortest day, giving you the opportunity for a leisurely breakfast and late start. The climb out of Whitby Bay involves 199 steps and takes you up to the old abbey ruins, and to St Mary’s church with its boat deck construction inside. The trail then follows the coastal cliffs once more, with good bird life, depending on the time of year! You then rejoin the Coast-to-Coast trail for the last few miles into Robin Hood's Bay. This little places drops steeply down to the sea and the Bay Hotel is a good place to sit with a beer on the ocean terrace, watching the sea and all those people celebrating that have just completed the Coast to Coast walk.

After a couple of easy days, you now have quite a long one to the seaside resort of Scarborough, certainly the largest settlement that you will visit on this tour. The route goes past the planned for but abandoned resort of Ravenscar where the Victorian street layouts can be detected where the grass has receded. At nearly 200 metres high, you will get possibly the most beautiful view of the Yorkshire coast. You then follow the cliffs gradually descending into Scarborough with its two sandy bays, castle remains on a headland and chances for swimming, ice cream etc. This is said to be the first English seaside resort, having long been associated with spring waters from the 1600s.

The last stretch of your walks meanders along behind Cayton Sands and then along the cliffs again to the calcareous grit stone promontory at Filey Brigg (also a nature reserve). If it is low tide, you can cross the sands to finish at Filey, otherwise you need to retrace your steps to get round to this pleasant fishing/resort town.

Arrangements end after breakfast.