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Cleveland Way Walk: 110 Miles in the Footsteps of Captain Cook

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The Cleveland Way Walk is a stunning 110-mile path (177 km) in North Yorkshire that follows a horseshoe shape through a diverse landscape of heather moorland, dramatic coastline, charming villages, and North York Moors National Park. 

It starts in the historic market town of Helmsley before taking you on an epic journey through the North York Moors before hugging the coastline to the seaside town of Filey.

The Cleveland Way Walk introduces you to a wealth of history and heritage that you can enjoy, which includes Helmsley Castle, The White Horse of Kilburn, Mount Grace Priory House & Gardens, Scarborough Castle, and much more.

Cleveland Way between Ravenscar and Scarborough

Highlights of the Cleveland Way National Trail

  1. Rievaulx Abbey – A stunning 12th-century Cistercian monastery ruin showcasing the architectural prowess of the medieval period.
  2. Roseberry Topping – A uniquely shaped hill offering breathtaking panoramic views of the surrounding countryside and moorland.
  3. Whitby – A historic seaside town with famous attractions such as Whitby Abbey, Captain Cook connections, and links to Bram Stoker’s Dracula.
  4. Robin Hood’s Bay – A picturesque fishing village with a rich smuggling history, charming narrow streets, stunning coastal views and dramatic cliffs.
  5. Scarborough – The final destination of the Cleveland Way. It’s a lively seaside resort with attractions like Scarborough Castle, the Rotunda Museum, and South Bay Beach.
Roseberry Topping hill, one of the scenic spots in the Cleveland Way Walk
Roseberry Topping

The Cleveland Way Walk is one of 16 national trails found in the UK.

Here’s a list of all the national trails in the UK: Cleveland Way, Cotswold Way, Glyndwr’s Way, Hadrian’s Wall Path, North Downs Way, Offa’s Dyke Path, Peddars Way and Norfolk Coast Path, Pennine Bridleway, Pennine Way, Pembrokeshire Coast Path, The Ridgeway, South Downs Way, South West Coast Path, Thames PathThe West Highland Way, Yorkshire Wolds Way. 


The Cleveland Way Walk 7-Day Itinerary 

It takes around 6 to 9 days to complete the 110 miles, but of course, this all depends on how long you want to spend on sightseeing and activities and how far you’re willing to walk each day.

I’ve hiked in the UK for 20 years, have experience in teaching outdoor education and have walked the Cleveland Way, so you’re in good hands. I’ll share the highlights, point out tricky or technical sections if there are any, and share my favorite accommodations for walkers each day. Let’s get started!

One of the great things about this hike is nearly anyone can do it. There’s hardly any elevation; the only tricky part is navigating the marshlands.

With that said, let’s take a look at the day-to-day:

Cleveland Way footpath

Day 1: Walk From Helmsley To Osmotherley

  • Start Point: Helmsley
  • Distance: 22 miles (36 km)
  • Total Ascent: 544 m (1,788 ft)
  • Finish Point: Osmotherley

The first day of the hike starts with an epic day. It starts from the Historic market town of Helmsley.

You’ll start your hike with an easy woodland walk across the stunning landscapes of the Rye Valley shortly after passing the ruins of Helmsley Castle.

Hemsley Castle as seen from the Cleveland Way walk
Hemsley Castle

You’ll start your hike with an easy woodland walk across the stunning landscapes of the Rye Valley shortly after passing the ruins of Helmsley Castle.

My highlight of the day was taking extra time to explore Kilburn White Horse (a chalk horse carved into the hill) just before Sutton Bank.

The views from Sutton Bank are stunning on a clear day, so take a few pics before heading to your final destination at the village of Osmotherley.

For accommodation, I recommend;  The Queen Catherine Hotel, Paddock View, or Vane House Bed & Breakfast.

Osmotherley, one of the walks in Cleveland Way and Coast to Coast walk national trails
Osmotherley

Day 2: Walk From Osmotherley To Clay Bank Top

  • Start Point: Osmotherley
  • Distance: 12 miles (18 km)
  • Total Ascent: 455 m (1,496 ft)
  • Finish Point: Clay Bank Top

From Osmotherley, you’ll skirt around the outside of Arncliffe Wood, ascending 150 meters to the top of Shephard Hill.

From there, you’ll traverse Holey Moor, where you’ll get stunning views of the village of Great Broughton and beyond as you reach the top of Cringle Moor.

Cleveland Way near Clay Bank Top
Cleveland Way between Clay Bank and Wainstones

Eventually, you’ll come to the B1257 road, where you’ve reached the area of Clay Bank Top. However, camping is the only accommodation there.

If camping isn’t your preferred accommodation, then I recommend heading north to Great Broughton.

They have a few accommodation options, including Whitehouse or Wainstones Hotel.

Day 3: Walk From Clay Bank Top To Captain Cook’s Monument

  • Start Point: Clay Bank Top
  • Distance: 12 miles (19 km)
  • Total Ascent: 217 m (712 ft)
  • Finish Point: Captain Cook’s Monument
Captain Cook's Monument as seen from Cleveland Way walk
Captain Cook’s Monument

Today is a relatively easy walk, but don’t worry; tomorrow will compensate for that. The day starts with a sharp descent toward Cleveland Hills (200 meters).

Eventually, you’ll reach the historical monument of Ingleby Incline. It’s where the Victorians were tasked with transporting ironstone, which was brought across the moors in Rosedale.

You’ll then slog across two moors: Battersby Moor and Kildale Moor. Shortly after, you’ll briefly stop at the village of Kildale, where you can continue to Captain Cook’s Monument.

The monument was erected in memory of the famous circumnavigator who lived in Great Ayton as a wrong boy.

If you’re looking for somewhere to stay for the night, and don’t want to camp, head back to Kildale, where you can stay at The Old Rectory Kildale. Or stop your day and start from there the next day, but be warned, tomorrow is already a long day. 

Day 4: Walk From Captain Cook’s Monument to Staithes

  • Start Point: Captain Cook’s Monument
  • Distance: 21 miles (34 km)
  • Total Ascent: 401 m (1,322 ft)
  • Finish Point: Staithes
Staithes village, one of the Cleveland Way walks

Today will be a long day of hiking, so hopefully, you got a good night’s sleep. You will be breaking away from the Yorkshire Moors and heading to the coastal path for a fantastic day of hiking.

You’ll start climbing to the top of Roseberry Topping (320 meters), a distinctive hill thanks to its half-cone jagged cliff.

Once you’ve conquered this hill, you’ll walk through the woods until you reach the town of Skeleton and then onto the town of Saltburn by the Sea.

From there, you’ll follow the east coast, where you can celebrate with a dip in the sea at the charming sleepy village of Staithes.

For accommodation, I recommend Felicity Cottage, Keel Lodges, Roraima House, or the Captain Cook Inn.

Day 5: Walk From Staithes To Robin Hood’s Bay

  • Start Point: Staithes
  • Distance: 18.2 miles (29.5 km)
  • Total Ascent: 348 m (1,142)
  • Finish Point: Robin Hood’s Bay
Robin Hood’s Bay, one of the Cleveland Way walks and Coast to Coast walks in England

Today you will be walking from one charming village to the next; it truly is an excellent section of the Cleveland Way.

Other than the coast and the charming coastal towns you pass, there’s not much more to see. One of the highlights was stopping off in Whitby for some fish and chips before continuing to Robin Hood’s Bay.

There are plenty of places to stay in Robin Hood’s Bay Village, including North Ings, Lee Side, Thackwood B&B, or Victoria.

Day 6: Walk From Robin Hood’s Bay To Scarborough

  • Start Point: Robin Hood’s Bay
  • Distance: 14 miles (22.5 km)
  • Total Ascent: 355 m (1,165 km)
  • Finish Point: Scarborough
Scarborough, one of the Cleveland Way walks

You’ll start the day by walking by Stoupe Beck Sands (a small beach) below 130 steep steps. Shortly after, you’ll arrive at the coastal village of Ravenscar, where you’ll finish off the last section of the North York Moors National Park.

After a few more hours of hiking, you’ll arrive at the town resort of Scarborough. Make sure you check out Scarborough Castle for a taste of history.

For accommodation, I recommend checking out the Granby Hotel, The Crown Spa Hotel, Delmont, or the Travel Lodge.

Day 7: Walk From Scarborough To Filey

  • Start Point: Scarborough
  • Distance: 11.5 miles (18.5 km)
  • Total Ascent: 79 m (262 ft)
  • Finish Point: Filey
Filey, last walk of the Cleveland Way national trail
Filey Brigg

It’s your final day of walking the Cleveland Way, and you’ll depart Scarborough along the beaches before getting onto the rocky terrain.

One of the highlights of today was passing Filey Brigg Country Park, a 9-acre park that offers beautiful views across the coast.

Once you arrive at Filey, you can either stay the night at Westreach Filey or Kev’s Cottage or get the train back to wherever you came from.


Cleveland Way Marker
Cleveland Way marker for long distance walk

Where to Stay on the Cleveland Way

Arrival Day: Helmsley

Day 1: Osmotherley. Our Recommendations: The Queen Catherine Hotel, Paddock View, or Vane House Bed & Breakfast.

Day 2: Clay Bank Top. Our Recommendations: Whitehouse or Wainstones Hotel.

Day 3: Captain Cook’s Monument. Our Recommendation: The Old Rectory Kildale.

Day 4: Staithes. Our Recommendations: Felicity Cottage, Keel Lodges, Roraima House, or the Captain Cook Inn.

Day 5: Robin Hood’s Bay. Our Recommendations: North Ings, Lee Side, Thackwood B&B, or Victoria.

Day 6: Scarborough. Our Recommendations: Granby Hotel, The Crown Spa Hotel, Delmont, or the Travel Lodge.

Day 7: Filey. Our Recommendations: Westreach Filey or Kev’s Cottage.


Yellow fields seen along the Cleveland Way walk

Frequently Asked Questions About the Cleveland Way

Are There Any Similar Hikes In The UK?

A few hikes in the UK are similar to the Cleveland Way Walk. The Jurassic Coast covers the same stunning coastal views. The Coast to Coast Walk is another great choice.

What Is the Start and Finish Point of the Cleveland Way?

Officially it starts in the town of St Bees and finishes at Robin Hood’s Bay, but you could easily do it the other way round.

When Is The Best Time To Walk the Cleveland Way?

Ideally, you should go in the summer. You’ll be passing through a lot of moorlands, and when it’s raining, it makes it very tricky. It will be busier, but it’s definitely worth avoiding the boggy ground.

Who Will Enjoy Walking the Cleveland Way?

This beautiful path is suitable for many active people since there’s not a lot of elevation gain.

Nature lovers will enjoy the diverse landscapes of classic moorland scenery, dramatic coastline, and charming woodland.

History enthusiasts will appreciate the numerous historical sites the trail passes, including Rievaulx Abbey, Mount Grace Priory, and Whitby Abbey, providing a fascinating insight into the region’s rich past.

Where To Get Food & Drink When Walking the Cleveland Way?

While there are towns and villages you can stop for a bit to eat in, we always recommend carrying some hiking snacks with you, though, in case you get hungry and aren’t near a village.

You’ll also want to have a good hiking breakfast before you head out each day.

What Gear Do I Need To Bring on the Cleveland Way Walk?

Here’s our list of recommended trekking gear for a multi-day walk like this. Of special note is buying clothing made from Merino wool, which is perfect for English weather, especially if you’re doing the walk in spring or fall.

Plus, I like to bring a good hiking book so I have something to read in the evenings (usually on my Kindle) and record the day in my hiking journal.

And for the ladies who still want to look good while doing this route, check out our hiking makeup tips.


More Information on Walking the Cleveland Way Walk

Guidebooks are great sources of information, like this guidebook which includes a route planner, and route maps if you’re planning on doing it by yourself.


Conclusion: 

The Cleveland Way Walk is an excellent choice for walkers who don’t want a lot of elevation gain, who love nature, especially coastal scenery, and who appreciate history.

Cleveland Way Walk: 110 Miles in the Footsteps of Captain Cook

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