image of the Cleveland Way UK walk with a gat and wooden signpost on hillside with hills and trees in the distance

Cleveland Way

110 miles Moderate

The Cleveland Way was designated as a National Trail in 1969 and runs for 110 miles. It starts in the pretty market town of Helmsley, near the ruins of its medieval castle, passes across the heather-clad North York Moors, before meeting the coast at Saltburn-by-the-Sea. The North Sea section then takes you down via Whitby and its spectacular ruined abbey to the finish point at Filey Brigg.

The Cleveland Way offers moderate terrain with are some steep sections where the path skirts the North York Moors before joining the North Sea coast. The coastal section is relatively easy, with the occasional dip down to sea level and climb back up. Urra Moore is the highest point on the path at 1489 ft high. The Path is well signposted with the National Trails’ acorn symbol.

North Yorkshire Moors


  • Day 1   Helmsley to Sutton Bank – 10.5 miles
  • Day 2   Sutton Bank to Osmotherley – 11.75 miles
  • Day 3   Osmotherley to Clay Bank – 11 miles
  • Day 4   Clay Bank to Kildale – 9.5 miles
  • Day 5   Kildale to Saltburn-by-the-Sea – 15 miles
  • Day 6   Saltburn-by-the-Sea to Sandsend – 17 miles
  • Day 7   Sandsend to Robin Hood’s Bay – 10.5 miles
  • Day 8   Robin Hood’s Bay to Scarborough – 13.75 miles
  • Day 9   Scarborough to Filey – 11 miles

You can choose to walk Helmsley to Saltburn-by-the-Sea, then south down the coast to Filey, however we can also arrange a Filey start point if you would prefer. Helmsley is about 25 miles from York where there is a mainline train station. Filey is served by a local train station that goes to Hull.


A price for a holiday walking the Cleveland Way is from £995 per person (based upon 2 people sharing). This includes:

  • Personalised itinerary for walking the on a self-guided basis over 9 days
  • 10 nights’ bed & breakfast accommodation on a double or twin room basis (this includes B&B for the night before you start and the day you finish)
  • Taxis for drop-off/pick-up where the B&B is not within easy walking distance of the path
  • Baggage transfer for one bag per person between each night’s B&B
  • Advice on travel arrangements to and from the start and finish points
  • Ordnance Survey Explorer maps which can be downloaded onto the OS App
  • Harvey Waterproof Map for the Cleveland Way
  • Standalone Safe Seat Plan Guarantee for each traveller issued by the Travel Trust Association
  • Kit checklist – covering boots & socks, clothes & waterproofs, and other useful kit
  • Helpline – you can call us at any time

Solo traveller price £1320 as most B&Bs do not have single rooms and charge almost as much for one person as for two.

Key Information:

  • Time of Year: This walk can be done at any time of year, although we recommend between April and October for the best weather conditions and longer daylight hours.
  • Terrain: The terrain is moderate for much of its length with relatively level paths and a few steep climbs and descents. Moreover, the walking surfaces are generally good, although they can be muddy in places depending upon the time of year.
  • Way marking: The route is well signposted with the National Trails’ acorn symbol.
  • Bed & Breakfast: We always aim to book good quality B&B accommodation as near as possible to the path yet, despite its popularity, there are relatively few B&Bs on the path itself or within easy walking distance. This means that sometimes the only option is to book B&Bs that are away from the path and arrange pick-up/drop-offs by taxi.
  • Refreshments: Compared with some other routes, this walk is actually quite good for places en route to get a cup of coffee (or a bacon butty or cake!) without having to deviate from the path. However, whether these will be open depends on the time of year, day of the week and time you happen to be passing.

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