What is this 7-day itinerary?
Seven days fits the whole Cleveland Way into a week by walking the first day straight through to Osmotherley. That day is long, but once you are up on Sutton Bank the edge only undulates. The Cleveland Hills still get a short day of their own, and the coast goes fast, with long days to Staithes and Robin Hood's Bay.
Read the Cleveland Way guide for the whole trail.
Will this 7-day split work for you?
- Fit walkers with a week, who are used to days of about 20 miles (32 km).
- Walkers who still want the Cleveland Hills as a short day, not squeezed into a long one.
- Three long days: choose a plan with more nights if you have not walked long days in a row before.
Fitness & effort
Three days are long: Helmsley to Osmotherley, Newton under Roseberry to Staithes and Staithes to Robin Hood's Bay, each 19 miles (30 km) to 21 miles (34 km). The first is steady ground. The other two end on steep cliff path. You need to be fit for long days in a row, with the hard Cleveland Hills day in between.
Your 7-day route on the map
Toward Filey
Helmsley to Filey in 7 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 → Clay Bank Top | 10.9 mi (17.6 km) | Clay Bank Huts (opens in a new tab) |
| Day 3 | Clay Bank Top → Newton under Roseberry | 13.8 mi (22.1 km) | The King's Head Inn (opens in a new tab) |
| Day 4 | Newton under Roseberry → Staithes | 19.6 mi (31.5 km) | Coble Cottage Staithes (opens in a new tab) |
| Day 5 | Staithes → Robin Hood's Bay | 18.9 mi (30.5 km) | North Ings - Robin Hood's Bay (opens in a new tab) |
| Day 6 | Robin Hood's Bay → Scarborough | 15.7 mi (25.3 km) | Clifton Hotel Scarborough (opens in a new tab) |
| Day 7 | Scarborough → Filey | 8.1 mi (13.1 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)
The long first day, and the gentlest ground of the three long ones. After Rievaulx and the climb to Sutton Bank, the Hambleton edge and the drove road undulate north for hours, never severe. Cold Kirby has no facilities, so pack the day's food in Helmsley. Osmotherley's pubs are a welcome sight.
Example stay Vane House Bed and Breakfast Osmotherley
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Day 2
Osmotherley to Clay Bank Top
10.9 mi (17.6 km) ↑ 840 m (2,750 ft) ↓ 710 m (2,350 ft)
A short day that is the hardest walking of the trip, and it comes straight after the longest. The flagged path rises and falls over five moors, with views north over Teesside and down into the dales. Lord Stones café is the one place to eat. There is no bed at Clay Bank Top, so the night is at Clay Bank Huts nearby, which offer a pick-up.
Example stay Clay Bank Huts (opens in a new tab)
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Day 3
Clay Bank Top to Newton under Roseberry
13.8 mi (22.1 km) ↑ 570 m (1,850 ft) ↓ 550 m (1,800 ft)
A middle day before the long coast. The climb out of Clay Bank leads onto Urra Moor and its broad heather. Kildale is the first place to eat, and it has a station if you need it. Captain Cook's Monument is the last high point, then the walk down to Newton under Roseberry, where the night is.
Example stay The King's Head Inn (opens in a new tab)
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Day 4
Newton under Roseberry to Staithes
19.6 mi (31.5 km) ↑ 720 m (2,350 ft) ↓ 1,030 m (3,400 ft)
A long day from moor to sea. Roseberry Topping and Guisborough Woods take the morning, and farmland brings you down to Saltburn. Buy food and water there. The steep drop into Skinningrove and the climb to Boulby come late, on a cliff edge that is unfenced in places.
Example stay Coble Cottage Staithes (opens in a new tab)
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Day 5
Staithes to Robin Hood's Bay
18.9 mi (30.5 km) ↑ 630 m (2,050 ft) ↓ 590 m (1,950 ft)
Another long day, with every bay a drop and a climb. Runswick Bay and Sandsend come before Whitby, where St Mary's church and the abbey stand above the harbour. Stock up in Whitby, because Robin Hood's Bay has no large shop. After the abbey the cliff top eases into the village.
Example stay North Ings - Robin Hood's Bay (opens in a new tab)
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Day 6
Robin Hood's Bay to Scarborough
15.7 mi (25.3 km) ↑ 560 m (1,850 ft) ↓ 600 m (1,950 ft)
A roller coaster of short climbs after two long days. The walker who described this stretch as 17 miles of small ups and downs called it reasonably challenging. Hayburn Wyke's wooded bay has a waterfall and a pebble beach, and its wooden steps are slippery after rain. Scarborough Castle marks the end.
Example stay Clifton Hotel Scarborough (opens in a new tab)
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Day 7
Scarborough to Filey
8.1 mi (13.1 km) ↑ 250 m (800 ft) ↓ 210 m (700 ft)
The gentlest finish on the coast. Regular trains and buses link Scarborough and Filey, so the day can be as unhurried as you like. The cliffs above Cayton Bay lead to Filey Brigg, a birdwatchers' paradise at the end of the trail. Its rocks 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. A walk off the path to a bed is extra.
Toward Helmsley
Filey to Helmsley in 7 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 → Scarborough | 8.1 mi (13.1 km) | Clifton Hotel Scarborough (opens in a new tab) |
| Day 2 | Scarborough → Robin Hood's Bay | 15.7 mi (25.3 km) | North Ings - Robin Hood's Bay (opens in a new tab) |
| Day 3 | Robin Hood's Bay → Staithes | 18.9 mi (30.5 km) | Coble Cottage Staithes (opens in a new tab) |
| Day 4 | Staithes → Newton under Roseberry | 19.6 mi (31.5 km) | The King's Head Inn (opens in a new tab) |
| Day 5 | Newton under Roseberry → Clay Bank Top | 13.8 mi (22.1 km) | Clay Bank Huts (opens in a new tab) |
| Day 6 | Clay Bank Top → Osmotherley | 10.9 mi (17.6 km) | Vane House Bed and Breakfast Osmotherley |
| Day 7 Longest | Osmotherley → Helmsley | 21.3 mi (34.3 km) | Helmsley |
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Day 1
Filey to Scarborough
8.1 mi (13.1 km) ↑ 210 m (700 ft) ↓ 250 m (800 ft)
A gentle start from Filey Brigg along the cliffs above Cayton Bay. This coast is slipping into the sea, so stay on the signed path. Many places in Scarborough want a two-night stay, so book early.
Example stay Clifton Hotel Scarborough (opens in a new tab)
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Day 2
Scarborough to Robin Hood's Bay
15.7 mi (25.3 km) ↑ 600 m (1,950 ft) ↓ 560 m (1,850 ft)
Leave Scarborough under the castle and walk north to Hayburn Wyke, a wooded bay with a waterfall. Its steps are slippery when wet. From Ravenscar the path dips to sea level twice before Robin Hood's Bay.
Example stay North Ings - Robin Hood's Bay (opens in a new tab)
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Day 3
Robin Hood's Bay to Staithes
18.9 mi (30.5 km) ↑ 590 m (1,950 ft) ↓ 630 m (2,050 ft)
An easy cliff top carries you north to Whitby and its abbey. Buy what you need in the town, because the afternoon's bays at Sandsend and Runswick are steep. Staithes is a quiet harbour at the end.
Example stay Coble Cottage Staithes (opens in a new tab)
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Day 4
Staithes to Newton under Roseberry
19.6 mi (31.5 km) ↑ 1,030 m (3,400 ft) ↓ 720 m (2,350 ft)
Staithes to Saltburn is the cliff half, with the steep climb out of Skinningrove early on. Eat in Saltburn before turning inland to the woods. Roseberry Topping is a hard pull near the end, so skip the spur if you are tired.
Example stay The King's Head Inn (opens in a new tab)
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Day 5
Newton under Roseberry to Clay Bank Top
13.8 mi (22.1 km) ↑ 550 m (1,800 ft) ↓ 570 m (1,850 ft)
Climb from Newton under Roseberry to Captain Cook's Monument, then down through Kildale and up onto the open moor. There is nothing to buy after Kildale, so carry the afternoon's food. Clay Bank Huts are a short walk from the top, with a pick-up on offer.
Example stay Clay Bank Huts (opens in a new tab)
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Day 6
Clay Bank Top to Osmotherley
10.9 mi (17.6 km) ↑ 710 m (2,350 ft) ↓ 840 m (2,750 ft)
From Clay Bank Huts, the climb to the Wainstones opens a run of five moors. The flags keep each climb steady, but there are a lot of them, so rest at Lord Stones. The views reach north over Teesside all afternoon.
Example stay Vane House Bed and Breakfast Osmotherley
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Day 7 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
7-day itinerary FAQ
Can I walk the Cleveland Way in a week?
Yes, if you are fit for long days. This plan walks Helmsley to Osmotherley in one go, keeps the Cleveland Hills short, then covers the coast in four days. Three of the seven days are 19 miles (30 km) to 21 miles (34 km).
Which day is the hard one?
Osmotherley to Clay Bank Top has the hardest climbing, over five moors, but it is short. Helmsley to Osmotherley is the longest, on steadier ground. Newton under Roseberry to Staithes is nearly as long, and its cliffs at Skinningrove and Boulby come at the end.
Can I download a GPX for the 7-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 7-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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