8-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)

   The woods and ponds of Nettledale are pretty but can be muddy after rain, and the climb out of the Rye Valley to the escarpment is never steep. Rievaulx Abbey and its café are a short detour. Enjoy the short day to Kilburn below the White Horse, because the coast days on this plan are long.

   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)

   Climb back past the White Horse and walk north on the Hambleton edge, a broad track shared with cyclists and riders. It is open to the weather, with Gormire Lake far below and no food on the way, so carry lunch from Kilburn. Osmotherley has pubs, a café and a hostel, and a good night matters before the hills.

   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)

   Five moors in a row, with the climbs coming in short bursts. Look for the old alum, jet and ironstone workings on the slopes, and for the Wainstones, a jumble of sandstone blocks near the end. Lord Stones café is the only stop. The night is at Clay Bank Huts, a short walk off the path, and they offer a pick-up.

   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)

   Above Clay Bank Top, Urra Moor is broad heather at the highest point of the walk. The old railway line beyond is shared with cyclists and riders, and Blowarth Crossing is the remotest point on the trail. Kildale has food and a station. The walk down to Newton under Roseberry adds to the day.

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

5. Day 5 Longest

   Newton under Roseberry to Staithes

   9–10 h 19.6 mi (31.5 km) ↑ 720 m (2,350 ft) ↓ 1,030 m (3,400 ft)

   The long day of this plan, from moor to sea. Roseberry Topping and Guisborough Woods fill the morning, and farmland brings you to Saltburn. Buy food and water there, because the steep drop into Skinningrove and the climb to Boulby come on tired legs. Staithes, an old fishing village, is the night.

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

6. Day 6

   Staithes to Robin Hood's Bay

   8–9 h 18.9 mi (30.5 km) ↑ 630 m (2,050 ft) ↓ 590 m (1,950 ft)

   The second long day in a row. Every bay from Runswick to Sandsend is a steep drop and a climb back out. Kettleness, between them, slipped into the sea in 1829. Whitby is halfway and the place to stock up, because Robin Hood's Bay has no large shop. After the abbey the cliff top eases into the old smugglers' village.

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

7. Day 7

   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)

   Shorter than the two days before, but full of short climbs. Boggle Hole and Stoupe Beck drop to sea level, and Ravenscar sits at the top of a long, gradual rise. The Hayburn Wyke Inn is close to the path in the afternoon, and hourly buses run along this coast if your legs give out before Scarborough.

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

8. Day 8

   Scarborough to Filey

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

   An easy last day on the cliffs. Past Holbeck, a hotel slid into the sea in 1994, and the coast there is still moving, so keep to the signed path. The trail ends out on Filey Brigg, where the rocks are slippery when wet. Filey has trains for the journey 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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