What is this 6-day itinerary?
Six days is a fast Cleveland Way that keeps every bed on or beside the path. The moors go by in two long days, the second over the Cleveland Hills and Urra Moor to Kildale. Then a short day under Roseberry Topping catches your breath before three long days on the cliffs.
Read the Cleveland Way guide for the whole trail.
Will this 6-day split work for you?
- Very fit, experienced walkers who are used to days of 20 miles (32 km) or more.
- Walkers who want no long walks off the path to a bed: every night is on or close to the line.
- Not a first long walk. Start from the 9-day if you are unsure.
Fitness & effort
Five of the six days are around 17 miles (27 km) to 21 miles (34 km). The second crosses the five moors of the Cleveland Hills and Urra Moor, the hardest walking of the trail. The coast is a run of short, steep climbs. Walk this only if you are used to long hill days back to back.
Your 6-day route on the map
Toward Filey
Helmsley to Filey in 6 days
Helmsley to Filey, the way most walk, with the wind more often behind you and the moors before the sea.
| Day | Stage | Distance | Overnight / destination |
|---|---|---|---|
| Day 1 Longest | Helmsley → Osmotherley | 21.3 mi (34.3 km) | Vane House Bed and Breakfast Osmotherley |
| Day 2 | Osmotherley → Kildale | 20.3 mi (32.7 km) | The Old Rectory Kildale (opens in a new tab) |
| Day 3 | Kildale → Slapewath | 10.3 mi (16.6 km) | The Fox & Hounds Hotel (opens in a new tab) |
| Day 4 | Slapewath → Runswick Bay | 17.3 mi (27.9 km) | The Royal Hotel (opens in a new tab) |
| Day 5 | Runswick Bay → Ravenscar | 18.7 mi (30.0 km) | Ravenscar House Bed & Breakfast (opens in a new tab) |
| Day 6 | Ravenscar → Filey | 20.3 mi (32.7 km) | Cleveland Way Finish |
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Day 1 Longest
Helmsley to Osmotherley
21.3 mi (34.3 km) ↑ 680 m (2,250 ft) ↓ 580 m (1,900 ft)
A long first day on steady ground. Rievaulx and the climb out of the Rye Valley come early, then the Hambleton edge undulates north on broad tracks, never severe. The visitor centre at Sutton Bank has refreshments, and after it there is nothing until Osmotherley. Carry the afternoon's food.
Example stay Vane House Bed and Breakfast Osmotherley
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Day 2
Osmotherley to Kildale
20.3 mi (32.7 km) ↑ 1,090 m (3,600 ft) ↓ 1,080 m (3,550 ft)
The hardest day of the plan: the Cleveland Hills and Urra Moor together. The flags rise and fall over five moors, and you will feel every climb by Clay Bank. Fill your bottles at Lord Stones café, because the high moor beyond has no shelter and nothing to buy. Kildale is on the path, so the day ends at the bed.
Example stay The Old Rectory Kildale (opens in a new tab)
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Day 3
Kildale to Slapewath
10.3 mi (16.6 km) ↑ 510 m (1,650 ft) ↓ 560 m (1,850 ft)
A short day to recover after two long ones. Captain Cook's Monument stands on Easby Moor, and Roseberry Topping is a steep spur with a wide view. The rest is Guisborough Woods, the longest forestry on the Way, sheltered and easy on the feet. The Fox and Hounds at Slapewath is a short way from the path.
Example stay The Fox & Hounds Hotel (opens in a new tab)
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Day 4
Slapewath to Runswick Bay
17.3 mi (27.9 km) ↑ 660 m (2,150 ft) ↓ 770 m (2,550 ft)
Down to the sea at Saltburn and onto the cliffs. The drop into Skinningrove and the climb to Boulby, England's highest east-coast cliff, are steep, and the edge is unfenced in places. Staithes, with its pubs and cafés, is the place for lunch. Runswick Bay is a few more miles on.
Example stay The Royal Hotel (opens in a new tab)
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Day 5
Runswick Bay to Ravenscar
18.7 mi (30.0 km) ↑ 770 m (2,550 ft) ↓ 610 m (2,000 ft)
A long coast day, and the bays at Sandsend and beyond are short, sharp drops. Whitby is halfway, the place to stock up, because Robin Hood's Bay has no large shop. After its steep lanes the path climbs gradually to Ravenscar, and those last miles are felt at the end of a long day.
Example stay Ravenscar House Bed & Breakfast (opens in a new tab)
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Day 6
Ravenscar to Filey
20.3 mi (32.7 km) ↑ 530 m (1,750 ft) ↓ 670 m (2,200 ft)
A long last day. Hayburn Wyke's wooded bay and slippery steps come first, then Scarborough, the place to eat. The cliffs to Filey are easier, though the coast there is still slipping into the sea, so keep to the signed path. The trail ends out on Filey Brigg, on rocks that are slippery when wet.
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.
Toward Helmsley
Filey to Helmsley in 6 days
The same nights, starting at Filey. The coast comes first and the Cleveland Hills near the end.
| Day | Stage | Distance | Overnight / destination |
|---|---|---|---|
| Day 1 | Filey → Ravenscar | 20.3 mi (32.7 km) | Ravenscar House Bed & Breakfast (opens in a new tab) |
| Day 2 | Ravenscar → Runswick Bay | 18.7 mi (30.0 km) | The Royal Hotel (opens in a new tab) |
| Day 3 | Runswick Bay → Slapewath | 17.3 mi (27.9 km) | The Fox & Hounds Hotel (opens in a new tab) |
| Day 4 | Slapewath → Kildale | 10.3 mi (16.6 km) | The Old Rectory Kildale (opens in a new tab) |
| Day 5 | Kildale → Osmotherley | 20.3 mi (32.7 km) | Vane House Bed and Breakfast Osmotherley |
| Day 6 Longest | Osmotherley → Helmsley | 21.3 mi (34.3 km) | Helmsley |
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Day 1
Filey to Ravenscar
20.3 mi (32.7 km) ↑ 670 m (2,200 ft) ↓ 530 m (1,750 ft)
A long opening day, starting out on Filey Brigg and following the cliffs above Cayton Bay. Scarborough is halfway and the place for lunch. Hayburn Wyke's steep wooded steps come before the climb to Ravenscar.
Example stay Ravenscar House Bed & Breakfast (opens in a new tab)
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Day 2
Ravenscar to Runswick Bay
18.7 mi (30.0 km) ↑ 610 m (2,000 ft) ↓ 770 m (2,550 ft)
Ravenscar to Robin Hood's Bay is a gradual descent with two sharp drops to sea level. Whitby makes a natural lunch stop in the middle of the day. Sandsend's bay is the last steep drop before Runswick.
Example stay The Royal Hotel (opens in a new tab)
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Day 3
Runswick Bay to Slapewath
17.3 mi (27.9 km) ↑ 770 m (2,550 ft) ↓ 660 m (2,150 ft)
The coast half of the day comes first, along cliffs that are unfenced and eroding in places, so keep to the signed path. Boulby's long descent ends in the steep drop to Skinningrove. At Saltburn you turn inland toward the woods.
Example stay The Fox & Hounds Hotel (opens in a new tab)
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Day 4
Slapewath to Kildale
10.3 mi (16.6 km) ↑ 560 m (1,850 ft) ↓ 510 m (1,650 ft)
The forestry of Guisborough Woods keeps you sheltered all morning. On Highcliff Nab and Roseberry Topping the plain opens up below you, so take the spur if the day is clear. Kildale has a station if you need to leave the walk.
Example stay The Old Rectory Kildale (opens in a new tab)
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Day 5
Kildale to Osmotherley
20.3 mi (32.7 km) ↑ 1,080 m (3,550 ft) ↓ 1,090 m (3,600 ft)
Urra Moor comes first, broad heather at the highest point of the walk, open to every wind. From Clay Bank the five moors roll west to Osmotherley, each a climb and a drop. Lord Stones café sits halfway through them.
Example stay Vane House Bed and Breakfast Osmotherley
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Day 6 Longest
Osmotherley to Helmsley
21.3 mi (34.3 km) ↑ 580 m (1,900 ft) ↓ 680 m (2,250 ft)
Broad tracks along the Hambleton edge carry you south for most of the day, with little to climb and nothing to buy. The drop off Sutton Bank and the woods past Rievaulx bring you to Helmsley's tearooms and pubs.
Finish Helmsley
6-day itinerary FAQ
Is six days realistic?
For a very fit walker, yes, and it is sold at this length. Five of the six days are long, and the second crosses the Cleveland Hills and Urra Moor together. If you have not walked several long hill days in a row, choose the 7-day or longer.
Why Kildale and Slapewath?
Both have beds on or close to the path, so no day ends with a long walk down to a bed. Kildale is the first village with beds after Urra Moor. Slapewath splits the walk from Kildale to the coast with a short day.
Can I download a GPX for the 6-day Cleveland Way?
Yes. Open this itinerary in the planner (free, no account). Download a full-route GPX or per-day files for Garmin, Komoot, or your phone. You can export the preset unchanged or edit overnight stops first.
Personalise this itinerary
This 6-day itinerary is ready as it stands. Open it in the planner to keep these stops, or change where you sleep, then download the GPX for your watch or phone.
Open in planner Back to the comparison
Full-trip and per-day GPX files. Free, no account.
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