Cleveland Way

The Cleveland Way National Trail is a long distance footpath that broadly follows the perimeter of the North York Moors National Park from the attractive market town of Helmsley to the seaside resort of Filey. From Helmsley you cross wild heather moorland as you walk towards the coast at Saltburn-by-the-Sea. The remainder of the trail follows the coastline south, passing through beautiful fishing villages and towns and spectacular beaches and cliff tops including Robin Hood's Bay and the popular seaside resorts of Scarborough and Whitby.

  • 102 miles / 164 kms
  • 17086 feet / 5208 metres
  • 6-9 days
  • Helmsley - Filey

The Cleveland Way is within the ability of all reasonably fit walkers. The trail is challenging in places, particularly across the moors in winter, but the path is well signposted so navigation is simple. Most people walk the trail in a clockwise direction starting in Helmsley and finishing at Filey sands. However, you can of course walk in the opposite direction.


The walking distances each day will vary depending on the accommodation you choose each night. Large groups may need to use hotels and inns in towns and villages nearby. The hotels and inns you stay with can provide a packed lunch, which you collect on departure. The long days on the first section across the moors can be shortened by not leaving the trail to descend to villages for your accommodation. Instead you can wild camp on the moors - but this option requires you to carry additional gear of course.

Helmsley, Cleveland Way, North Yorkshire National Park, England
7 Days

Day 1 - Helmsley to Osmotherley - 19 miles / 31 kms
Day 2 - Osmotherley to Great Broughton - 11 miles / 17 kms
Day 3 - Great Broughton to Guisborough - 20 miles / 33 kms
Day 4 - Guisborough to Staithes - 18 miles / 29 kms
Day 5 - Staithes to Robin Hood's Bay - 17 miles / 28 kms
Day 6 - Robin Hood's Bay to Scarborough - 16 miles / 25 kms
Day 7 - Scarborough to Filey - 10 miles / 15 kms

Sandsend, Cleveland Way, North Yorkshire National Park, England
8 Days

Day 1 - Helmsley to Osmotherley - 19 miles / 31 kms
Day 2 - Osmotherley to Great Broughton - 11 miles / 17 kms
Day 3 - Great Broughton to Great Ayton - 16 miles / 26 kms
Day 4 - Great Ayton to Saltburn-by-the-Sea - 14 miles / 23 kms
Day 5 - Saltburn-by-the-Sea to Whitby - 18 miles / 30 kms
Day 6 - Whitby to Ravenscar - 10 miles / 16 kms
Day 7 - Ravenscar to Scarborough - 11 miles / 18 kms
Day 8 - Scarborough to Filey - 10 miles / 15 kms

There are very good public transport options to most parts of the The Cleveland Way trail. There are train stations at York, Malton, Thirsk, Middlesbrough, Great Ayton, Whitby, Scarborough and Filey. The start of the trail at Helmsley cannot be reached directly by train but there are connecting bus services from York, Malton and Scarborough. If you are parking your car at the start you can return to it from Filey via a train to Scarborough and then a bus to Helmsley.


Harvey Map

The whole trail on one convenient water resistant sheet at a scale of 1:40,000

Ordnance Survey Map

Book of maps which shows the route on Ordnance Survey Explorer map tiles (1:25,000)

Trailblazer Guidebook

Advice on hotels, pubs, restaurants, cafes, attractions, local history and much more

GPS File: Cleveland Way

Download GPS points of the whole trail from Helmsley to Filey

Hotels & Inns

We have listed some of the better hotels and inns with links to TripAdvisor where you can read customer reviews and check prices and availability. If you like an early start, when booking accommodation check the time breakfast is served in the morning. All should be able to provide packed lunches. For those finishing late, check when evening meals end.