10-day Cleveland Way itinerary

1. Day 1

   Helmsley to Kilburn

   3–4 h 8.4 mi (13.6 km) ↑ 360 m (1,200 ft) ↓ 140 m (450 ft)

   Leave Helmsley under its castle and walk through Nettledale's woods. Rievaulx Abbey is a short detour, and the climb to Sutton Bank is steady. James Herriot called the view from the bank over the Vale of York the finest in England. Kilburn is down the hill below the White Horse, so tomorrow begins with a climb.

   Example stay The Forresters Arms

2. Day 2

   Kilburn to Osmotherley

   5–6 h 12.8 mi (20.7 km) ↑ 320 m (1,050 ft) ↓ 430 m (1,400 ft)

   Up past the White Horse again and north along the Hambleton edge. The path near Oakdale has been rebuilt against erosion, and the drove road beyond is broad and easy. There is no food on it, so carry lunch. Osmotherley is the last village before the hills, with pubs, a café and camping.

   Example stay Vane House Bed and Breakfast Osmotherley

3. Day 3

   Osmotherley to Clay Bank Top

   5–6 h 10.9 mi (17.6 km) ↑ 840 m (2,750 ft) ↓ 710 m (2,350 ft)

   The guides call it the hardest day, and it feels longer than its miles: climb, descend, climb again. In mist the tops have little shelter, so carry a map or GPS. Lord Stones café is the only stop. The night is at Clay Bank Huts, a short walk off the path, with a pick-up on offer.

   Example stay Clay Bank Huts (opens in a new tab)

4. Day 4

   Clay Bank Top to Newton under Roseberry

   6–7 h 13.8 mi (22.1 km) ↑ 570 m (1,850 ft) ↓ 550 m (1,800 ft)

   Longer than it looks, because the beds at both ends are off the path. On Urra Moor, look out for two old stones by the path, one carved with a hand and one with a face. There is nothing to buy until Kildale. Captain Cook's Monument is the last climb before the walk down to Newton under Roseberry.

   Example stay The King's Head Inn (opens in a new tab)

5. Day 5

   Newton under Roseberry to Saltburn-by-the-Sea

   4–5 h 10.7 mi (17.2 km) ↑ 360 m (1,200 ft) ↓ 640 m (2,100 ft)

   The last of the moors, and a day of views. Roseberry Topping is a steep spur with a wide panorama, and Highcliff Nab looks out over Guisborough and the plain. The woods are full of junctions, so watch the acorns. Farmland leads down past Skelton to Saltburn and the sea.

   Example stay Saltburn House (opens in a new tab)

6. Day 6

   Saltburn-by-the-Sea to Staithes

   4–5 h 8.9 mi (14.3 km) ↑ 360 m (1,200 ft) ↓ 390 m (1,300 ft)

   A short day that is steeper than its miles. The drop into Skinningrove and the climb to Boulby, the highest cliff on England's east coast, come in the first half, and the edge is unfenced in places. Carry water from Saltburn. Staithes has pubs, cafés and the rest of the afternoon.

   Example stay Coble Cottage Staithes (opens in a new tab)

7. Day 7

   Staithes to Whitby

   5–6 h 12.0 mi (19.2 km) ↑ 360 m (1,200 ft) ↓ 360 m (1,200 ft)

   Runswick Bay and Sandsend are the two steep drops of the day, each with a climb back out. Between them, Kettleness slipped into the sea in 1829, so keep to the signed path. Take your time, because the night is in Whitby. The 199 steps up to St Mary's church and the abbey can wait for the evening.

   Example stay Haven Guesthouse Whitby - RF (opens in a new tab)

8. Day 8

   Whitby to Robin Hood's Bay

   3–4 h 7.0 mi (11.2 km) ↑ 270 m (900 ft) ↓ 230 m (750 ft)

   Barely half a day. Climb to the abbey that inspired Bram Stoker's Dracula, then follow an easy cliff top south to Robin Hood's Bay. Buy anything you need in Whitby, because the village has no large shop. You will have the afternoon for its steep lanes.

   Example stay North Ings - Robin Hood's Bay (opens in a new tab)

9. Day 9 Longest

   Robin Hood's Bay to Scarborough

   7–8 h 15.7 mi (25.3 km) ↑ 560 m (1,850 ft) ↓ 600 m (1,950 ft)

   The longest day of the plan, and a roller coaster of short climbs. The path drops to sea level at Boggle Hole and Stoupe Beck before rising to Ravenscar, where seals can sometimes be seen. Hayburn Wyke's wooden steps are slippery after rain. The small climbs add up before Scarborough.

   Example stay Clifton Hotel Scarborough (opens in a new tab)

10. Day 10

    Scarborough to Filey

    3–4 h 8.1 mi (13.1 km) ↑ 250 m (800 ft) ↓ 210 m (700 ft)

    A gentle last day on the cliffs above Cayton Bay. Past Knipe Point, bungalows have been lost to the sea, and the coast is still moving, so keep to the signed path. The trail ends out on Filey Brigg, where the rocks are slippery when wet. Filey, a Victorian resort, has trains home.

    Finish Cleveland Way Finish

Cross-check: Cleveland Way trail information on National Trails . The trail body lists 9 days for the 109 miles (175 km). Distances on the cards are measured along the trail on our line. A walk off the path to a bed is extra.

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