Guided Trail on the Cleveland Way complete itinerary

Complete Trail – 7 nights

108 miles. 11 - 20½ miles and up to 3,200 feet of ascent in a day.

Day 1: Arrival day

Day 2: Helmsley to Osmotherley - Leaving Whitby, we travel to Helmsley Place to start our walk along the Cleveland Way. Our first objective is Rievaulx Bridge; the famous abbey is half a mile from here and , unfortunately there is not time for us to pay a visit. We continue through Nettle Dale to Cold Kirby where we join the Cote Moor Road to the Hambleton Inn. We then follow the ancient boundary line of Casten Dyke and emerge on top of the spectacular escarpment of Sutton Bank. We continue north along the escarpment via Whitestone Cliff and above Gormire Lake to Cleave Dyke and Sneck Yate Bank Top. From here we walk to High Paradise Farm then continue north to Whitestones and Hambleton End, with the impressive view of Black Hambleton. We next drop down to Jenny Brewster Moor and the reservoir in pretty Oak Dale. Afterwards we follow the Cleveland Way past White House and climb into Osmotherley village. Distance: 20¼ miles with 1,700 feet of ascent

Day 3: Osmotherley to Kildale - From Osmotherley we continue our walk along Ruebury Lane to Beacon Hill, the starting of the Lyke Wake Walk. The next stretch is one of the finest of the whole Cleveland Way. The most noteworthy being the summit of Hasty Bank and its Wainstones. After crossing the road at Clay Bank Top, we head up Carr Ridge to Urra Moor, and at Round Hill we reach the highest point in the Cleveland Hills. We continue on to Bloworth Crossing, where we say goodbye to the Lyke Wake Walk. From here we head north to Greenhow Bank, before crossing Battersby Moor and down to Kildale. Distance: 20½ miles with 3,200 feet of ascent
 
Day 4: Kildale to Skinningrove - Returning to Kildale village we continue our walk over Coate Moor to visit Captain Cook’s Monument. Dropping down to Gribdale Gate we climb again on to Ayton Bank and Black Bank. The energetic amongst us may wish to climb Roseberry Topping with magnificent views in all directions. We continue east over Hutton Moor to Highcliff Nab, eventually descending to Slapewath Bridge. We will climb up Spring Bank to Airy Hill then through Skelton, over Skelton Beck at Jackdaw Scar, at last reaching the coast at Saltburn-by-the-Sea. The moors-walking is now behind us and we can look forward to glorious seascapes and awesome sights of high cliffs pounded by relentless seas. We take the cliff path above Old Saltburn and continue to the old ironstone mining village of Skinningrove. Distance:  17½ miles with 1,700 feet of ascent; with Roseberry Topping option, 18½ miles with 2,150 feet of ascent

Day 5: Skinningrove to Whitby - We rejoin the cliff path at Skinningrove and onto Hummersea Cliff. Our Cleveland Way walk will continue over Boulby Cliff, passing the site of one of the best-preserved alum works in England to reach Staithes, a picturesque fishing village. Our walk continues along the cliffs to Runswick Bay with its pretty fishermen’s cottages. We now take to the sands before climbing steeply on to the cliff path again, eventually reaching the farmstead at Kettleness. From here we follow the cliff path to Sandsend, the last mile of which is along the old Middlesbrough−Scarborough railway line. We conclude our day by walking along the sands and into Whitby and Larpool Hall. Distance: 17½ miles with 1,550 feet of ascent

Day 6: Whitby to Scalby Mills - Walking from Larpool Hall we resume our Cleveland Way Walk from the top of the famous 199 steps at the Abbey Church in Whitby, along the cliffs to Robin Hood’s Bay. We shall descend through this attractive village, then continue along the coast up to the cliff-top village of Ravenscar. From here we follow the cliffs to Hayburn Wyke and finally Scalby Mills near Scarborough, where we finish our walk for the day. Distance 20 miles with 1,400 feet of ascent
 
Day 7: Scalby Mills to Filey - Returning to Scalby Mills we continue on the coast path to Scarborough. Our route continues to Cornelian Bay and along Frank Cliff to arrive at Cayton Bay. If the tide is right we shall be able to walk along the sands to the water works and then climb to the cliff path. Nearly at journey’s end, we continue along the coast path to Filey Brigg where a stone sculpture marks the end of the Cleveland Way. Distance: 11¼  miles with 700 feet of ascent

Day 8: Departure day