National Trail · North Yorkshire

Cleveland Way

A 109-mile walk round the North York Moors and down the Yorkshire coast, from Helmsley to Filey Brigg.

109Miles

175Kilometres

7–11Days

The Cleveland Way is a captivating 109-mile (175 km) National Trail in North Yorkshire, offering a blend of rugged moorland, dramatic coastal cliffs and sweeping pastoral landscapes.

It showcases some of the most scenic vistas in the North York Moors and along the North Sea coastline, making it a favourite among walkers for its diversity and beauty. The trail starts in Helmsley, loops round the moors and then follows the coast south to Filey.

Terrain and Duration

Terrain: The trail varies, starting with heather moorland, passing through wooded areas, and continuing along dramatic coastal cliffs and beaches. The path includes some steep ascents and descents, particularly along the coastal section.
Typical Duration: Most walkers complete the trail in about 9 to 11 days.

Highlights of the Cleveland Way

Helmsley Castle: Starting point with ruins dating back over 900 years.
Rievaulx Abbey: Near the start, the impressive ruins of a 12th-century Cistercian abbey.
The Moors: Sweeping views of the North York Moors, known for their expansive heather moorland.
Roseberry Topping: A distinctive hill with panoramic views, often a favorite spot for photos.
Whitby: A historic seaside town known for its association with Bram Stoker’s Dracula and the beautiful Whitby Abbey.
Robin Hood’s Bay: A picturesque former fishing village, with narrow winding streets and charming cottages.
Scarborough Castle: Offers spectacular views over Scarborough and the coast.
Filey Brigg: The trail concludes at this prominent peninsula, with views across Filey Bay.

Planning Your Walk

Accommodation: There is a variety of accommodation along the route, including camping sites, youth hostels, bed and breakfasts, and hotels. Advance booking is essential, especially during the busy summer months.
Transportation: Access to public transportation is good at several points along the way, such as Helmsley, Whitby, and Scarborough, making it possible to tackle the trail in sections if preferred.
Supplies: There are numerous towns and villages along the route where you can resupply. However, portions of the moorland sections are quite remote, so carrying sufficient water and snacks for these parts is advisable.
Waymarking: The Cleveland Way is well-marked with the acorn symbol typical of National Trails. However, carrying a map or GPS device is recommended for safety and navigation.
Weather and Clothing: Weather can be highly variable, particularly along the coast. It’s important to have waterproof clothing and sturdy walking boots. The coastal wind can be strong, so extra layers are advisable.

Tips for Walking the Cleveland Way

Physical Preparation: The varied terrain requires a good level of fitness, especially for handling long distances and the steep coastal paths.
Respect the Environment: The route passes through sensitive environments, including Sites of Special Scientific Interest (SSSI). Stick to the path to avoid damaging flora and disturbing wildlife.
Safety: Notify someone of your plans and expected return times, particularly when walking remote sections.
Local Culture and History: Engage with the local culture by visiting museums, historical sites, and trying local foods, particularly seafood in the coastal towns.

Walking the Cleveland Way offers not just physical exercise but also a journey through some of the most historically rich and visually stunning landscapes in Yorkshire. Whether you are looking for the tranquility of the moors or the dramatic beauty of the coastline, this trail delivers an unforgettable experience.

Interactive Map of Cleveland Way

Route map for Cleveland Way by William Nash on plotaroute.com

7 Day Walking Itinerary.

Stage	Start Point	Distance	Ascend / Descend
Day 1	Helmsley to Osmotherley	21	1420
Day 2	Osmotherley to Great Broughton	11
Day 3	Great Broughton to Guisborough	20	2499
Day 4	Guisborough to Runswick Bay	16
Day 5	Runswick Bay to Robin Hood’s Bay	14
Day 6	Robin Hood’s Bay to Scarborough	14
Day 7	Scarborough to Filey	11

7 Day Walking – Cleveland Way

9 Day Walking Itinerary.

Stage	Start Point	Distance	Ascend / Descend
Day 1	Helmsley to Sutton Bank	10	1420
Day 2	Sutton Bank to Osmotherley	11.5
Day 3	Osmotherley to Clay Bank	11	2499
Day 4	Clay Bank to Kildale	9.3
Day 5	Kildale to Saltburn	14.7
Day 6	Saltburn to Sandsend	17.5
Day 7	Sandsend to Robin Hoods Bay	10
Day 8	Robin Hoods Bay to Scarborough	12
Day 9	Scarborough to Filey	10.5

9 Day Walking – Cleveland Way

11 Day Walking Itinerary.

Stage	Start Point	Distance	Ascend / Descend
Day 1	Helmsley to Kilburn	11	1420
Day 2	Kilburn to Osmotherley	13
Day 3	Osmotherley to Great Broughton	11	2499
Day 4	Great Broughton to Great Ayton	12
Day 5	Great Ayton to Guisborough	9
Day 6	Guisborough to Saltburn-By-The-Sea	6
Day 7	Saltburn-By-The-Sea to Runswick Bay	12
Day 8	Runswicks Bay to Whitby	8
Day 9	Whitby to Ravenscar	10
Day 10	Ravenscar to Scarborough	10
Day 11	Scarborough to Filey	11