Complete Guide to Walking the Cleveland Way

Cleveland Way is located in northern England and the trail in ancient Cleveland runs for more than a hundred miles. The trail along dramatic coastline offers fabulous views and fishing villages that are tucked into tiny coves on the heather moorland. This is your chance to explore the untouched landscapes of Northern England, the region where dinosaurs once roamed freely. 

The development of Cleveland Way started way back in the 1930s, and it was in the fifties when a formal proposal to create routes and trails was submitted.  The trail was opened for the public towards the end of the 20th century. One can take the trail which is marked with the National Trail acorn symbol along its length, in either direction. There is a central section that leads from Helmsley while the coastal section follows the coast from Saltburn. One will come across varying landscapes as they wander across the region. They can explore picturesque old shops and historic villages. There are important abbeys and churches on the way that are major attractions for the pilgrims who look for peace and solace here. Enjoy impressive views from the highest points over the Cleveland Hills.

If this is your first trip to Cleveland Way, then just follow the complete guide on this page to learn more about the different rails and routes to explore in Cleveland Way.

How to reach Cleveland Way
One can arrive in England by air or by sea or by road. The nearest international airport to Cleveland Way is Manchester International and Leeds/Bradford Airport. From here one can take a bus or train. Hull is the nearest ferry terminal that runs daily ferries, and the York train station runs many train services to the region. One can also travel by road to the Cleveland Way and can feel free to park their car at car parks along numerous points along the Trail. Thus, as you can see, Cleveland Way is very easy and accessible to reach. 

Best time to go to Cleveland Way
Although one can enjoy the walk on the Cleveland Way, the best time to see the moorland is from August to September when the area is in full bloom.  Early summer and springtime are great to experience the trip while May and June are beautiful. Still, if you cannot visit during those months, you will still be rewarded with an extraordinary experience and spectacular views. so, go ahead and palm your visit based on your convenience.

Food and lodging
A lot relies on the kind of package you have chosen for your trail. Whatever you opt for, you can be sure that the accommodation lies as close as possible to the trail. However, on some of the remote areas, you may not have private facilities. If the accommodation is at a distance from the trail, transfers are provided for the trekkers. You would be served English breakfast each morning that consists of sausage, bacon, eggs, fruit, toast, cereals, tea or coffee.

What to pack?
Pack warm clothes and water for the trip. There is no need to bring a sleeping bag as most hostels will not allow you to do so. Your day pack should contain lunch, snacks, waterproofs, first-aid kit and any other personal items that you might need. You need good quality waterproof walking shoes and waterproof jacket and trousers. It is a must to wear comfortable clothes and wear a hat and gloves. It is advisable to carry a mobile phone although receptions might not be good in some of the mountainous regions.

A self-guided or independent walking holiday?

With an independent tour, you decide when to travel and at what pace. However, for the self-guided walking trip, there are fixed timings between March and October. you need to book the self-guided trip in advance and can walk during specific dates. The trips can take a minimum of 5 nights and a maximum of 10 nights. If you are on an independent trip, you should be confident about your trekking skills and know how to read maps. Walking the Cleveland way with an expert local guide is the best way to experience and enjoy the trail.

Different trekking routes of the Cleveland Way

The trekkers can pick from different routes based on daily itineraries on the Cleveland Way, and all these trips are between 22 to 28 miles.

  • Helmsley to Osmotherley– Enjoy the historic village of Helmsley and visit its picturesque old shops. Rievaulx Abbey ruins are worth visiting and the highlight of the trip. Enjoy the beautiful views from Sutton bank and follow the old drovers’ road to Black Hambelton. Your day will end at a quaint village, Osmotherley that is known for its old shops and pubs.

Rievaulx Abbey ruins

  • Osmotherley to Kildale – This is the most strenuous part of the walk as you go up and down the Cleveland Hill. Enjoy the stunning views of the deep valleys and moorland along the way. The steep climb will take you to the highest point on the walk, Urra Moor. Enjoy the views before descending to Kildale.
  • Kildale to Saltburn – The climb up Easby Moor to Captain Cooks is the first part of the walk, and it continues through farmland. Later, you reach the coastal town of Saltburn after going on a riverside path. Later, you walk along the sea and get prepared for the coastal section of the trail. 
  • Saltburn-by-the Sea to Robin Hood’s Bay- Your walk from Saltburn to Filey goes along the coast. Along the way, you pass dramatic sections as you climb up Hunt Cliff and go through Rock Cliff. Descend to the charming village of Staithes and reach the town, Whitby with a picturesque harbor. Make way to the picturesque Robin Hoods Bay after crossing those small beaches and platforms.


Robin Hood’s Bay

  • Robin Hood’s Bay to Filey – This is the final phase of the walk that will take you through Scarborough, a seaside town. Those untouched villages and busy beaches with traditional entertainment are sure to keep you impressed. Before reaching Filey, you can look back to reflect on your walking adventure as you gaze at those vibrant colors of South Cliff. 



Explore Cleveland Way with its range of itineraries and different treks based on your level of fitness. Be well prepared as you would be walking on hilly terrain. So, unless you enjoy an active lifestyle and good cardiovascular exercise, it can be difficult for you to complete the trail. Still, you can prepare in advance for the experience and ensure that you are fit and fine before embarking on the trip. As Cleveland Way trials are immensely popular with the locals as well as the tourists, make sure that you make your bookings well in advance, especially if you plan to take the trip in April/May or July/August.


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