The Cleveland Way National Trail

Whats included?

Your en-suite accommodation with breakfast

Help and on-going support before and during your walking holiday.

A walking itinerary (self-guided) covering places of historic significance or areas of outstanding natural beauty.

Transport to and from a walking location if needed.

The relevant Ordnance Survey map waterproofed

Trail guide cards

A detailed itinerary with recommended lunch breaks at select pubs, tearooms or cafes.

Local folklore, myths and things of historic relevance

Seasonal nature guide book or cards for identifying the abundance of wild flowers, trees and wildlife

Luggage transfers from each venue with guaranteed delivery before you arrive.

Emergency backup and support if needed.

Once you complete the walk we will pick you up and return you to Helmsley for your car or take you to Scarborough train station, this is part of our service at no extra charge.

Travel Information

The following travel information may come in useful when planning your trip.

By Air - The most convenient major city and international airports are Leeds-Bradford, Manchester and Durham Tees Valley.

By Rail – If you travel to York Station we pick you up and take you to Helmsley. Please note we only offer this service from York Station.

By Bus - Various bus services run to Helmsley and from Filey as an option.

From London - Trains run from London Kings Cross station to York on a regular basis.

Return To The Start – We will pick you up and take you to Helmsley to pick up your car or to Scarborough train station if travelling by train.

End of holiday: Filey

Full description

The Cleveland Way trail is a stunning self guided walking holiday situated within the North York Moors National Park. The Cleveland Way became England’s second national trail in 1969 and offers stunning moorland walking and breathe taking coastal encounters en-route to the finish at Filey Brigg.

Starting from the picturesque market town of Helmsley, the walk comprises of two distinctive landscapes, the first 60 miles focus on skirting round the largest open moorland in England – the North York Moors, taking in the amazing panoramic views from Sutton Bank, the Wainstones and Roseberry Topping before reaching the Yorkshire Heritage coastline at Saltburn by the Sea. This is Yorkshire’s coastline at its most raw and elemental. Leaving Saltburn you will head south for 50 miles to witness some of the most stunning coastal walking in England, experience Boulby Cliffs which at 656ft are the highest on England’s east coast, you will encounter beautiful bays and historic fishing communities at Staithes and Runswick Bay and Robin Hoods Bay which during the 18th century became the busiest smuggling community on the Yorkshire coastline.

Walk Yorkshire offer a variety of walking itineraries ranging from 7 days  to 11 days walking, however we remain flexible to customer needs and if required we will work with you to produce an itinerary for your group to suit your needs. Or if you decide on the moors section or coastal section then 5 days walking.

Cleveland Way –Coastal section, incorporating the Yorkshire Heritage Coastal Walk.

This is Yorkshire’s coastline at its most raw and elemental. Intimidating cliffs may tower over beautiful bays including Staithes and Runswick Bay. The breath taking views from the impressive Boulby Cliffs, which at 656ft (200m) are the highest on England’s east coast. Visit Whitby, the historic fishing port of Captain Cook and where his famous ship the Endeavour was built and sailed from. Robin Hood’s Bay with its many hiding places, bolt holes and secret passages made it the perfect location for smugglers. From RHB follow the coastline to the picturesque holiday resort of Scarborough before reaching your final destination at Filey Brigg.

Prices start from £500 for 6 nights – 5 days walking

Cleveland Way – Moors section

A walking holiday from Helmsley to Saltburn-by-the-Sea through the purple clad heather of the North York Moors.

Starting from the picturesque market town of Helmsley, the walk comprises of distinctive landscapes, this 60 mile walk circumnavigates the largest open moorland in England – the North York Moors taking in the amazing panoramic views from Sutton Bank, the Wainstones and Roseberry Topping before reaching the Yorkshire Heritage coastline at Saltburn by the Sea.

Prices start from £500 for 6 nights – 5 days walking

Highlights of the walk

Helmsley Castle

Rievaulx Abbey

The beautiful coastal villages of Staithes, Runswick Bay and Robin Hoods Bay

Boulby Cliffs an impressive 656ft high (200m) – walker’s paradise

Captain Cook Museum – a nostalgic trip back in maritime history

Whitby’s historical Abbey – Bram Stoker’s inspiration for the creation of Dracula

Yorkshire‘s unique Jet shops and Jet Museum

Traditional Yorkshire shops, café’s, tearooms and pubs all along this coastal walk with a great choice in Whitby.

Accomodation details

Your accommodation

One of the reasons our customers choose Walk Yorkshire is for our range of high-quality accommodation. So after a tiresome day on the hills where you stay is an important factor impacting on your overall walking experience.

The country hotels and pubs where you stay are individual, very friendly with excellent Yorkshire hospitality. Each one is situated on the route or very close to it with comfortable bedrooms and delicious local food and drinks to enjoy with dinner after your walk. Kevin, the Walk Yorkshire founder hand picks all the accommodation personally, some date back centuries and have their own tale to tell. On the Cleveland Way accommodation can be sparse so we have carefully selected a different country inn or hotel for you to stay every three or four days (depending on your itinerary).

On this particular trail you can enjoy the charms of an 18^th century grade 2 listed building where you will be well looked after, the rooms are furnished in a contemporary and calming colour palette to maximise rest and relaxation following a long days walking. Every hotel is uniquely designed and all our bedrooms have en-suite private bathrooms with modern facilities.

Price breakdown

We offer the following walking options for the Cleveland Way

Code               Tour                            Duration                     Difficulty                    Price per person  

CWAY1           Helmsley to Filey        8 nights,     7 days      Demanding                 £670   

CWAY 2          Helmsley to Filey        10 nights,   9 days      Moderate                     £840   

CWAY3           Helmsley to Filey        11 nights,  10 days     Moderate                     £920   

CWAY 4          Moors section only     6 nights     5 days      Moderate                     £500   

CWAY5           Coastal section only   6 nights      5 days     Moderate                     £500   

All prices shown are based upon two people sharing a room.

*For singles or groups of more than 10 wanting to book with us, please contact us via the online form here.