11-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)

   An easy first day, with time for Rievaulx Abbey in its valley. The path passes Cold Kirby, a village with no facilities, and the old Hambleton Down racecourse on the way to Sutton Bank. Kilburn is a short walk down from the White Horse, and tomorrow starts by climbing back to it.

   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)

   Back up to Sutton Bank and north on the Hambleton edge, where Gormire Lake lies far below. The drove road is broad but open to the weather, and the ground can be muddy on the way down into Osmotherley. There is nowhere to buy food, so carry lunch. The village has pubs, a café and a hostel.

   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 hardest walking on the Way, kept short. Mount Grace Priory is half a mile off the path as you leave Osmotherley, if you start early. Then the flags carry you over five moors to the Wainstones. Eat at Lord Stones, the one café on the hills. 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 below the ridge. The climb back to Clay Bank Top leads onto Urra Moor, broad heather and an old railway line to Blowarth Crossing, the remotest point on the trail. Kildale has food and a station. Captain Cook's Monument comes 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 Guisborough

   1–2 h 3.4 mi (5.5 km) ↑ 150 m (500 ft) ↓ 210 m (700 ft)

   A very short day, made for Roseberry Topping. It rises straight above the inn, and the steep climb to its summit, at 320 m, gives a wide view over the plain. The path then enters Guisborough Woods. Gisborough Priory is in the town below if you have the afternoon.

   Example stay Gisborough Hall Hotel (opens in a new tab)

6. Day 6

   Guisborough to Saltburn-by-the-Sea

   3–4 h 7.2 mi (11.7 km) ↑ 210 m (700 ft) ↓ 430 m (1,400 ft)

   Another short day. Back into the woods, then farmland past Skelton brings you to the sea at Saltburn. You arrive with the afternoon free for the pier and the Cliff Lift. Rest well, because tomorrow starts on the cliffs with the steep drop into Skinningrove.

   Example stay Saltburn House (opens in a new tab)

7. Day 7

   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 first day on the cliffs, but a steep one. Look for the Charm Bracelet sculpture past Saltburn, then the drop into Skinningrove and the climb to Boulby, above Europe's deepest mine. The edge is unfenced in places. Carry water from Saltburn. Staithes, an old fishing village, is the night.

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

8. Day 8

   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 day's two steep drops, each with a climb back out. Take it slowly, because Whitby is the night. Its abbey, which inspired Bram Stoker's Dracula, stands on the cliff above the harbour, and St Mary's church is up the 199 steps beside it.

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

9. Day 9

   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 along an easy cliff top. Robin Hood's Bay was a smugglers' village from 1700 to 1850, its houses nesting on the cliff edge. Buy what you need in Whitby, because the village has no large shop. You will have most of the day to explore its lanes.

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

10. Day 10 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. The drops to Boggle Hole and Stoupe Beck come first, then the climb to Ravenscar and its old alum works. Hayburn Wyke has a waterfall and a pebble beach, and steps that are slippery after rain. The small climbs add up before Scarborough Castle comes into view.

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

11. Day 11

    Scarborough to Filey

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

    An easy last day along the cliffs, where the coast is still slipping into the sea, so keep to the signed path. Filey Brigg, a rocky point out into the sea, is the finish and a birdwatchers' paradise. Its rocks are slippery when wet, so take care before you celebrate. 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), and says you may want longer. Distances on the cards are measured along the trail on our line. A walk off the path to a bed is extra.

11-day itinerary FAQ