What is this 5-day itinerary?
Five days is the fastest Cleveland Way we plan, and it asks a lot. Each day is about 20 miles (32 km) or more, and the second crosses the Cleveland Hills and Urra Moor before you rest. The reward is the whole horseshoe in a working week, from the heather of the moors to the cliffs of the coast.
Read the Cleveland Way guide for the whole trail.
Will this 5-day split work for you?
- Very fit, experienced walkers: every day is about 20 miles (32 km) or more.
- Walkers who want the whole trail in a working week, with no long walks off the path to a bed.
- Not a first long walk. A reply on a walkers' forum called five days too short.
Fitness & effort
Every day is 20 miles (32 km) to 24 miles (38.5 km), on rough moor and cliff path with many short, steep climbs. Day two crosses the five moors of the Cleveland Hills and Urra Moor in one go. You need to have walked long hill days back to back before, and to keep a steady pace on tired legs.
Your 5-day route on the map
Toward Filey
Helmsley to Filey in 5 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 | 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 Longest | Kildale → Staithes | 23.9 mi (38.5 km) | Coble Cottage Staithes (opens in a new tab) |
| Day 4 | Staithes → Ravenscar | 22.4 mi (36.0 km) | Ravenscar House Bed & Breakfast (opens in a new tab) |
| Day 5 | Ravenscar → Filey | 20.3 mi (32.7 km) | Cleveland Way Finish |
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Day 1
Helmsley to Osmotherley
21.3 mi (34.3 km) ↑ 680 m (2,250 ft) ↓ 580 m (1,900 ft)
The steadiest of the five days, and a good one to find your pace. After the climb to Sutton Bank, the Hambleton edge undulates north on a broad drove road, never severe. The visitor centre on the bank is the last place to buy food until Osmotherley, so carry the afternoon's. Keep something back for tomorrow's hills.
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 Cleveland Hills and Urra Moor in one push, the hardest day of the plan. Five moors rise and fall on stone flags, then the high moor is open heather with no shelter. Lord Stones café is the last place to eat and fill up before Kildale. 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 Longest
Kildale to Staithes
23.9 mi (38.5 km) ↑ 1,040 m (3,400 ft) ↓ 1,200 m (3,950 ft)
The longest day, from moor to sea. Captain Cook's Monument, Roseberry Topping and Guisborough Woods take most of it. Buy food and water in Saltburn, because the steep drop into Skinningrove and the climb to Boulby come late. Staithes, an old fishing village, is a welcome end.
Example stay Coble Cottage Staithes (opens in a new tab)
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Day 4
Staithes to Ravenscar
22.4 mi (36.0 km) ↑ 900 m (2,950 ft) ↓ 740 m (2,450 ft)
A long coast day of drops and climbs, first into Runswick Bay and then Sandsend. Stock up in Whitby, the coast's main town, because Robin Hood's Bay has no large shop. After it the path climbs gradually to Ravenscar on tired legs, and stopping there leaves the last day near 20 miles.
Example stay Ravenscar House Bed & Breakfast (opens in a new tab)
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Day 5
Ravenscar to Filey
20.3 mi (32.7 km) ↑ 530 m (1,750 ft) ↓ 670 m (2,200 ft)
The last long day. Hayburn Wyke's wooded bay has steep steps, slippery after rain, and Scarborough is the place to eat. The cliffs after it are gentler, past Holbeck, where a hotel slid into the sea in 1994. Filey Brigg is the end, 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 5 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 → Staithes | 22.4 mi (36.0 km) | Coble Cottage Staithes (opens in a new tab) |
| Day 3 Longest | Staithes → Kildale | 23.9 mi (38.5 km) | The Old Rectory Kildale (opens in a new tab) |
| Day 4 | Kildale → Osmotherley | 20.3 mi (32.7 km) | Vane House Bed and Breakfast Osmotherley |
| Day 5 | 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 Staithes
22.4 mi (36.0 km) ↑ 740 m (2,450 ft) ↓ 900 m (2,950 ft)
The cliff top runs north from Ravenscar to Robin Hood's Bay and on to Whitby. Whitby is the coast's main place to buy food. The afternoon bays at Sandsend and Runswick are short and steep, so pace yourself for them.
Example stay Coble Cottage Staithes (opens in a new tab)
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Day 3 Longest
Staithes to Kildale
23.9 mi (38.5 km) ↑ 1,200 m (3,950 ft) ↓ 1,040 m (3,400 ft)
Start with the cliffs, while your legs are fresh for the climb out of Skinningrove. Fill up in Saltburn, because the woods and moor beyond have little. Roseberry Topping is the last steep pull before you drop to Kildale.
Example stay The Old Rectory Kildale (opens in a new tab)
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Day 4
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 5
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
5-day itinerary FAQ
Is five days realistic?
Only for a very fit walker. It is sold at this length, but every day is about 20 miles (32 km) or more, and a reply on a walkers' forum called five days too short. If you are unsure, choose the 7-day or longer.
What is the hardest day?
Day two, Osmotherley to Kildale, has the most climbing: the five moors of the Cleveland Hills and then Urra Moor. Day three, Kildale to Staithes, is the longest, with the steep cliffs at Skinningrove and Boulby at its end.
Can I download a GPX for the 5-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 5-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.
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Full-trip and per-day GPX files. Free, no account.
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