Discover Yorkshire’s Cleveland Way  holiday cottages

Discover Yorkshire’s Cleveland Way

Julie Smith 28 April 2020

The Cleveland Way is one of England’s seven national walking trails and includes wide stretches of Yorkshire coast and countryside with an array of market towns and pretty villages to stop at along its glorious 109-mile route. This guide takes you through each section so you can plan your adventures - click on each heading to find out more.

Cleveland Way
Image: Tony Bartholomew


Starting in the market town of Helmsley, the Cleveland Way passes through the North York Moors National Park with some well-loved Yorkshire landmarks including the White Horse at Kilburn, the Wainstones, and Roseberry Topping to spot along the route. The waymarked national trail then heads along the clifftop paths of the gorgeous Yorkshire Coast with spectacular sea views to enjoy all the way from Saltburn to Filey. 

Discover Yorkshire's Cleveland Way

The Cleveland Way can be broken down into a selection of smaller routes and there’s lots to see and do along the way, from calling in a country pub for some tasty refreshments to passing through some of the UK's most popular seaside towns. 

Skip to:

Helmsley to Sutton Bank

Helmsley, the starting point of the Cleveland Way, is a charming little town with a medieval castle that’s within the boundaries of the North York Moors National Park. There’s lots to see and do in and around the historic cobbled market square and Helmsley highlights include:

  • The pretty Helmsley Walled Garden which is featured in The Secret Garden film
  • The impressive ruins of Cistercian monastery Rievaulx Abbey
  • An array of lovely tearooms, artisan bakeries and independent shops      

The section of the Cleveland Way from Helmsley to Sutton Bank also includes the Kilburn White Horse - a whopping turf-cut figure that’s 314 feet by 228 feet and dates back to 1857. The view from the top of Sutton Bank was described as England’s finest view by author James Herriot and the visitor centre here features a great adventure playground for families tackling the walk. 

Where to stay: Rose Cottage, a three-bedroom holiday home in Helmsley

Sutton Bank to Osmotherley

The stretch of the Cleveland Way National Trail from Sutton Bank to Osmotherley takes in peaceful countryside, rugged moorland and dramatic views as you cross through the unspoilt western reaches of the North York Moors National Park. Part of the route follows an ancient drover’s path that farmers would have once used to walk their cattle to market. Things to look out for include:

  • The tranquil Gormire Lake is a remnant of the ice age - a natural lake that formed over 20,000 years ago from glacial erosion 
  • A walker’s tea room at High Paradise Farm where you can stop for refreshments
  • White Mare Crag, a dramatic limestone formation that’s also known as the Whitestone Cliffs  

This walk ends in the pretty village of Osmotherley where you’ll find pubs, cafes, a fish and chip shop and lots of old-world country charm. There’s an ancient market cross on the village green and nearby Mount Grace Priory is the best preserved Carthusian monastery in the UK.

Where to stay: Isla Cottage, a two-bedroom holiday in Osmotherley

Kildale to Saltburn

The village of Kildale is located in the Esk Valley and served by a scenic railway line which travels to Whitby through the North York Moors. The first point of interest on this section of the Cleveland Way is Captain Cook’s Monument which sits on Easby Moor and was built in 1827 in memory of Yorkshire’s famous explorer. Other highlights on this section of the walk are:

  • Roseberry Topping a hill that has a distinctive witch’s hat shape and that’s well worth climbing if you have the energy
  • Guisborough Forest - pretty woodland that’s teeming with nature and has a special sculpture trail to follow
  • Reaching the top of the Yorkshire Coast at Saltburn - enjoy cliff top views then catch a funicular train down to the beach below

Saltburn is a handsome Victorian town that includes a historic pier and the oldest water balanced tramway in England. Once a year Saltburn hosts a food festival and there’s lots of places in town where you can stop for a tasty bite to eat. 

Where to stay: Hare House, a two-bedroom holiday home near Stokesley

Staithes to Runswick Bay

This delightful Cleveland Way walk starts in Staithes, a fishing village filled with colourful cottages that are transformed each year into hundreds of art galleries as part of the annual Staithes Festival. Children will recognise Staithes as the setting for CBBC’s Old Jack’s Boat and the village’s Cod & Lobster pub is a must-visit for their tasty crab sandwiches. 

  • Start the walk at the Captain Cook & Staithes Heritage centre to learn more about North Yorkshire’s famous sea captain
  • Look back towards Staithes as you head along the cliff-top path - it’s a perfect spot for a photo as the village is postcard pretty
  • Keep your eyes peeled for birdlife diving around the Port Mulgrave headland about halfway along the walk

Cleveland Way - Runswick Bay

The final section of the route circles around a rock promontory known as Crocodile Head due to its distinctive shape before arriving at the horseshoe-shaped Runswick Bay. This sleepy Yorkshire Coast village has small peaceful streets and quaint cottages including the last remaining traditional thatched coastguard’s cottage in Yorkshire.

Where to stay: The Retreat, a two-bedroom holiday home in Sandsend

Whitby to Robin Hood’s Bay

Discover Yorkshire's Cleveland Way

Enjoy some time is wonderful Whitby before setting off on this scenic coastal stretch of the Cleveland Way. Whitby is one of the most popular seaside towns around, famous for its gothic abbey that inspired Dracula and fish and chip shops selling the catch of the day straight from the fishing boats. Explore Whitby’s old town and find quirky shops selling everything from Whitby Jet to lucky glass ducks.   

  • Start the walk by climbing 199 steps to Whitby Abbey and enjoying the view over the harbour
  • Look out for Whitby lighthouse and foghorn station which is around 2 miles from the town 
  • Discover Kittiwakes nesting at May Wyke Hole and catch your first glimpse of Robin Hood’s Bay from Ness Point 

Cleveland Way - Robin Hoods Bay

There’s a steep walk down the cliff to the beach at Robin Hood’s Bay but along the way there’s a myriad of narrow streets and alleys with pubs, cafes and independent shops to explore. The higgledy-piggledy nature of the cottages meant the village was a haven for smuggling in the 1800s - today it all just adds to the charm of the bay.   

Where to stay: Hidden Gem, a one-bedroom holiday home by the beach at Robin Hood’s Bay.

Scarborough to Filey

Filey Brigg Cleveland Way

The final section of the Cleveland Way stays on the waymarked coastal pathway, starting in Britain’s original seaside resort - Scarborough. Take a stroll along the bustling South Bay promenade before heading onto the cliff top route. It’s worth stopping by the Scarborough Star Disk, which comprises 42 fibre optic stars as they can be seen in the Scarborough night sky.

Highlights of this final stretch of the Cleveland Way include:

  • Looking down over Cayton Bay - an expense of sandy beach that’s a top pick for both surfers and fossil hunters
  • Admiring the view across to the white cliffs of Flamborough, which in the summer months are home to tens of thousands of nesting seabirds
  • Getting your photo taken by the Cleveland Way marker at Filey Brigg which also marks the end of the Yorkshire Wolds Way

Cleveland Way

It’s worth spending some time exploring Filey which has one of Yorkshire’s best beaches with a wide expanse of golden sand. Head to Coble Landing and you can grab a cuppa and cake to reward yourself with as you watch the boats come and go from this historic slipway. Filey is also home to some gorgeous parks and gardens including Crescent Gardens which features a bandstand that’s often used for free summer concerts.

Where to stay: The Seashore, a two-bedroom holiday home in Filey

Cleveland Way food and drink

Cleveland Way Food and Drink

There are lots of great pubs and restaurants to try right across the Cleveland Way. Here are just some of our favourites that are worth calling in for refreshments:

  • Mannion & Co – a Helmsley bistro that serves seasonal food washed down with champagne served by the glass
  • The Golden Lion - an 18th-century inn located near Osmotherley’s market cross
  • The Kings Head Inn - a traditional country pub at the base of Roseberry Topping
  • Runswick Bay Tea Garden - a hidden gem of a tea room that pops up for the summer season
  • The Magpie Cafe - fresh fish and seafood in a restaurant that looks out across Whitby harbour
  • The Bramblewick Fish and Grill bistro in Robin Hood’s Bay is housed in a 17th-century building by the sea
  • The Boat Shed in Filey specialises in pizza, gin and cocktails - just right for a relaxing evening after completing your Cleveland Way walk 

Plan your Yorkshire getaway

Image: Chris J Parker / NYMNP


Has this inspired you to try and walk some of the Cleveland Way? Gorgeous Cottages have a selection of holiday cottages across the North York Moors and Yorkshire Coast which are ideal for accessing this well-loved National Trail.


Disclaimer: Whilst every effort has been made to ensure the accuracy of the information at the time of writing, please ensure you check carefully before making any decisions based on the contents within this article.

Like it? Share it...

Read more like this

The UK’s most magical stately homes for Christmas

Discover the most festive stately homes, castles and historic houses to visit this Christmas.

Ten of the best Yorkshire Christmas markets

Discover some of the best Christmas markets to visit in Yorkshire this December. Ideal for shopping, mince pies and getting you into the festive spirit!

Discover Yorkshire's wildflower meadows

Discover some of Yorkshire's briliant, biodiverse and specially protectd wildflowers meadows in beautiful locations such as Askrigg, Grassington and Muker.
The Travel Chapter Limited trading as Gorgeous Cottages is an appointed representative of ITC Compliance Limited which is authorised and regulated by the Financial Conduct Authority (their registration number is 313486) and which is permitted to advise on and arrange general insurance contracts as an intermediary.
The Travel Chapter Limited trading as Gorgeous Cottages | The Travel Chapter Limited is registered in England and Wales. | Registered office Travel Chapter House Gammaton Road Bideford EX39 4DF Company No. 02431506 | VAT reg: 143053210.