The Cleveland Way 7 Day Itinerary

For long distance hikers wanting a fresh challenge, the Cleveland Way could be just the answer you are looking for.

In 6 days of hiking, you will walk from Helmsley, the only market town in the North York Moors National Park to Filey, a bustling Yorkshire seaside town along Moorland tracks, and the beautiful Yorkshire coastline.

The Cleveland way was opened in 1969, and travels 100 miles in total. It traverses classic moorland scenery.

Get your camera out for panoramic views over the Cleveland Hills and the exceptionally beautiful fishing villages on the Yorkshire Coastline.

The route can easily be accessed by public transport, which encourages.

Who will love this long distance hike?

The Cleveland Way is ideal for all abilities. It does have some steep ascents and descents, but hikers of all abilities should be able to handle the route.

What we love about the Cleveland Way is its diversity of landscape.

Not only will you get to enjoy the spectacular Yorkshire Moors, but you will also walk along a very pretty section of the English coastline, abundant with wildlife and panoramic views.

The Itinerary

Day 1: Arrive in Helmsley
Day 2: Walk from Helmsley to Osmotherley – 36km
Day 3: Walk from Osmotherley to Clay Bank Top – 18km
Day 4: Walk from Clay Bank Top to Captain Cook’s Monument – 19km
Day 5: Walk from Captain Cook’s Monument to Staithes – 34km
Day 6: Walk from Staithes to Robin Hood’s Bay – 29.5km
Day 7: Walk from Robin Hood’s Bay to Scarborough – 22.5km
Day 8: Walk from Scarborough to Filey – 18.5km

Route Map

How to use this map

Click the button in the top left hand corner to view the accommodation. We have added individual accommodation layers for campsites, hostels, and B&B’s. You can click the red check marks to hide or show layers.

By clicking on any of the icons on the map you can get more information about the accommodation and often a link (affiliate) to book online.

If you click the star next to the title of the map, this map will be added to your Google Maps account. To view it, open Google Maps on your phone or computer and find ‘Your Places’ where you can see the map on your list.

Day 2:

Walk from Helmsley to Osmotherley – 36km

Your first day of walking will see you put on your boots and set off from Helmsley to Osmptherley. You will be walking 36km, and passing the National Trusts Rievaulx Abbey, a Cistercian abbey that was seized under Henry VIII of England in 1538. You will continue on towards Sutton bank, before heading north, passing the Hambleton Hills on your right, and passing through Arden Great Moor.

Where to Stay

Vane House offers a delightful B&B stay, with prices starting from £108.00. The historic Queen Catherine Hotel has outside seating, and rooms available from £110.00. For campers, Cote Ghyll Caravan Park & Campsite offer tent pitches and has a youth hostel on site.

Day 3:

Walk from Osmotherley to Clay Bank Top – 18km

After skirting the outside of Arncliffe wood you will ascent Shephard hill, before traversing along Holey Moor. Great views of Great Broughton and beyond await as you walk along the tops of Cringle Moor. You will eventually come to the B1257 road, where you have reached Clay Bank Top.

Where to Stay

You can book into the Buck Inn further down the road at Chop Gate, The Buck Inn offer a Complementary lift from Clay Bank car park for long-distance walkers at 4.00pm and a drop-off the following morning.

Beakhills Farm also offers comfortable accommodation and is half a mile off route. The farm also offers camping.

Day 4:

Walk from Clay Bank Top to Captain Cook’s Monument – 19km

From Clay Bank Top you will sharply descend East towards the Cleveland Hills. You will pass over Greenhow Moor which leads to Ingleby Moor. YOu will continue onto Battersby Moor, and Kildale Moor. After a brief visit to the Village of Kildale you will continue towards Captain Cook’s Monument.

Where to Stay

A little before Captain Cooks Monument, you will discover Kildale. It’s suggested you use Kildale as an overnight stop. For campers, you can stay in Kildale Barn, Byre & Campsite, alternatively, The Old Rectory B&B in the village have rooms from £75.00.

Day 5:

Walk from Captain Cook’s Monument to Staithes – 34km

A big day of walking awaits, as you start to break away from the Yorkshire Moors, towards the Yorkshire Coast. First, a climb (albeit as a diversion) to the top of Roseberry Topping, a distinctive hill in North Yorkshire with its half cone jagged cliff is in order. After head through Guisborough woods, then across farmland towards Skelton, and onto Saltburn by the Sea. From here you will be on the East Coast. Celebrate, dip in the sea, then head south towards the sleepy village of Staithes.

Where to Stay

Staithes has a good choice of B&B’s. The Royal George comes highly recommended serving good food, with rooms over the village and harbor and rooms from £80.50. If you are camping the Serenity Campsite offers pitches from £11.00 for a single backpacker.

Day 6:

Walk from Staithes to Robin Hood’s Bay – 29.5km

From one beautiful village to the next. You are in for a treat. From Staithes, follow the Coast Path. You will pass a few National Trust-owned sections of the path, attesting to their beauty. Pass through Runswick Bay, Stop for Fish and Chips, and continue following the path towards Whitby. Whitby has a lot of interest and is worth a stop, but if you would rather move through it, continue along the Coast Path towards Robin Hood’s Bay.

Where to Stay

The Villa in Robin Hoods Bay is one of the best B&B’s, alternatively, take a look at Aldersyde B&B with rooms from £90.00.

There are a couple of options for camping, but your best bet is Bayness Farm, which is just off the Coast Path, to the North of Robin Hood’s Bay.

Day 7:

Walk from Robin Hood’s Bay to Scarborough – 22.5km

Departing from Robin Hood’s Bay, you will pass Stoupe Beck Sands, towards Ravenscar. From Ravenscar pass Blea Wyke Point, and the Hayburn Wyke Hotel, before turning towards Hundale Point. From here continue straight South past a very rocky section of beach, and cliff tops towards Scalby Ness Rocks before you reach the tourist village of Scarborough.

Where to Stay

Scarborough is a very popular seaside village and therefore has countless B&B’s, hotels and Inns. The best way to book is to take a look at what’s available on

There are a lot of campsites in Scarborough but the only one in reasonable distance of the Path is the local Caravan and Camping Club site which has pitches available from £20.00.

Day 8:

Day 8: Walk from Scarborough to Filey – 18.5km

You will depart Scarborough and enjoy the long beaches before getting onto rockier terrain passing Black Rocks. Continue to Clayton Bay, and towards Filey Country park. Take a diversion to Filey Brigg which is accessible at low tide before heading another kilometre towards Filey.

Where to Stay

The Forge House B&B offers comfortable and affordable rooms close to the trail while campers may enjoy Filey Brigg campsite.