The Cleveland Way

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 a couple of nice pubs to visit. Accommodation: The Black Swan is a wonderful pub dating back to the 15th century. With an Elizabethan building on one end, a Tudor one to the other and a Georgian House in the middle, the Black Swan is wonderfully higgledly-piggledy, with bags of character.

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. A transfer has been arranged to pick you up from Sutton Bank and you will return to Helmsley for the night (included in cost).

After breakfast, you will be transferred back at Sutton Bank. 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. Accommodation: Vane House is a large old stone guesthouse. A friendly welcome is offered and all spacious rooms are ensuite.

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 to Great Broughton. Accommodation: Great Broughton - Wainstones Hotel, this present day structure has developed around a former dwelling dating from early 1700.

Transfer 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. Accommodation: Royal Oak Hotel this 18th century rural hostelry is at the heart of the village. Original features include the beamed ceilings and welcoming log fires, which add to the charm and character of this traditional inn.

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. Accommodation: The Victoria Guesthouse is a family run guesthouse is situated only a few hundred yards from the beach.

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! It is difficult to secure 1 night stays in Runswick Bay so we will book a 2 night stay in Whitby. You can easily move between Runswick Bay & Whitby on the bus (own expense) or alternatively we would be happy to organise a return taxi transfer for you (own expense). Accommodation: Chiltern Guesthouse is a small seaside BB situated close to the harbour and beach. Of course this is a busy town and alternative accommodation will be used.