Cleveland Way

The 110 mile Cleveland Way was the second ever designated National Trail after the Pennine Way. This walk of two distinct halves begins in the attractive market town of Helmsley on the southern edge of the North York Moors. You will first follow sandstone escarpments, traverse wild heather moors and cross deep cut forested valleys, before leaving the hills for the coast at Saltburn. The second half of the route is a magnificent cliff-top coastal stride out, passing through pretty fishing villages, the picturesque home of Captain Cook, and a famous seaside resort before reaching journey's end at Filey.

Prices are per person based on twin share and include all accommodation in twin share rooms on bed & breakfast basis, luggage transfer, information pack including map & guidebook and our emergency contact.

Single rooms are available. We only apply a supplement for single accommodation when there is a direct cost to us and we cap this at a maximum of £25 per night. Solo walkers pay a supplement of £8 per night, plus any single supplement which may be required.

Entire Route Options

Walking the Cleveland Way in 7 stages is an option if you need to fit the walk within a single week. On this itinerary there are some long days and considerable accumulations of ascent and is only suitable for experienced walkers.

Arrive at Helmsley and check in.
Day 1 Helmsley to Osmotherley 22* miles
Day 2 Osmotherley to Clay Bank Top 11½ miles
Day 3 Clay Bank Top to Roseberry 14 miles
Day 4 Roseberry to Staithes 18½ miles
Day 5 Staithes to Robin Hoods Bay 18 miles
Day 6 Robin Hoods Bay to Scarborough 15 miles
Day 7 Scarborough to Filey 11 miles
Depart Filey
*includes 2½ mile diversion to White Horse

Walking the Cleveland Way in 9 stages is our recommended option for anyone used to Long Distance Path walking. On this itinerary the daily stages are between 10 and 15 miles with daily accumulated ascent in the region of 2000 - 2500ft.

Arrive at Helmsley and check in.
Day 1 Helmsley to Sutton Bank 10½* miles
Day 2 Sutton Bank to Osmotherley 11½ miles
Day 3 Osmotherley to Clay Bank Top 11½ miles
Day 4 Clay Bank Top to Kildale 10 miles
Day 5 Kildale to Saltburn-by-the-Sea 14½ miles
Day 6 Saltburn-by-the-Sea to Runswick Bay 11½ miles
Day 7 Runswick Bay to Robin Hoods Bay 14½ miles
Day 8 Robin Hoods Bay to Scarborough 15 miles
Day 9 Scarborough to Filey 11 miles
Depart Filey
*includes 2½ mile diversion to White Horse

Walking the Cleveland Way over 10 stages is our favourite option and should suit most walkers. On this itinerary the coastal section is split into shorter stages with stops at Staithes, Whitby, Robin Hoods Bay and Scarborough to make the most of this delightful and interesting leg of the walk

Arrive at Helmsley and check in.
Day 1 Helmsley to Sutton Bank 10½* miles
Day 2 Sutton Bank to Osmotherley 11½ miles
Day 3 Osmotherley to Clay Bank Top 11½ miles
Day 4 Clay Bank Top to Roseberry 14 miles
Day 5 Roseberry to Saltburn-by-the-Sea 10½ miles
Day 6 Saltburn-by-the-Sea to Staithes 8 miles
Day 7 Staithes to Whitby 11½ miles
Day 8 Whitby to Robin Hoods Bay 6½ miles
Day 9 Robin Hoods Bay to Scarborough 15 miles
Day 10 Scarborough to Filey 11 miles
Depart Filey
*includes 2½ mile diversion to White Horse

One-week Sections

The Cleveland Way splits itself naturally into two halves. The western half is packed with interest as you traverse the boundary of the North Yorks Moor National Park and over the Hambleton and Cleveland Hills. This section has a wide variety of scenery from farmland, woodland, river valleys, sandstone edges, and wild open moors. Of historical interest along the way are Rievaulx Abbey, the White Horse of Kilburn and Captain Cook's memorial as well as the picturesque market towns of Helmsley and Osmotherly.

Arrive at Helmsley and check in.
Day 1 Helmsley to Sutton Bank 10½* miles
Day 2 Sutton Bank to Osmotherley 11½ miles
Day 3 Osmotherley to Clay Bank Top 11½ miles
Day 4 Clay Bank Top to Roseberry 14 miles
Day 5 Roseberry to Saltburn-by-the-Sea 10½ miles
Depart Saltburn-by-the-Sea
*includes 2½ mile diversion to White Horse

The eastern half of the Cleveland way follows the coast from Saltburn to Filey. On this section you walk along cliff-tops, across secluded bays, through picturesque fishing villages, passing the Gothic ruins of Whitby Abbey, charming Robin Hoods Bay, and the famous seaside resort of Scarborough.

Arrive at Saltburn-by-the-Sea and check in.
Day 1 Saltburn-by-the-Sea to Staithes 8 miles
Day 2 Staithes to Whitby 11½ miles
Day 3 Whitby to Robin Hoods Bay 6½ miles
Day 4 Robin Hoods Bay to Scarborough 15 miles
Day 5 Scarborough to Filey 11 miles
Depart Filey

The price includes:

  • All accommodation in twin/double rooms (with private bathroom where available) in guest houses, inns or hotels
  • All breakfasts
  • Luggage transfer between hotels
  • A Wandering Aengus information pack containing all necessary maps, a current guide book, laminated locator maps for each night's accommodation, and our own weather-proof 'info cards' with local information - including locations and opening times of restaurants, cafes, ATMs, supermarkets etc.
  • Our emergency contact number

Not included:

  • Lunches and evening meals (we provide full details of your options)
  • Extra costs incurred through using escape routes or abandonment of the itinerary
  • Miscellaneous personal expenses such as drinks etc.

Our Accommodation:

As keen walkers ourselves we appreciate the importance of the place you put your feet up and rest your head in at the end of each day. We very carefully select our accommodations whether they be a cosy pub, family run guest house, or established town centre hotel. We choose places directly on the route or within easy walking distance of it and if we ever have to transfer you because of limited availability, we will always contact you to discuss this and never just leave you to find out later. We provide comfortable, clean and warm twin or double rooms, with private bathroom wherever available. Single occupancy of rooms is also available for a supplementary cost.

Meals:

Breakfast at your accommodation is included in the holiday price. In most cases your accommodation will serve dinner and will be able to prepare a packed lunch for you. Sometimes this will have to be arranged in advance and we will let you know if this is the case. Alternatively you can use our detailed notes to make your own dining and lunch arrangements using local restaurants, cafes and supermarkets.

HELMSLEY: There are buses to Helmsley from Pickering, Middlesborough, Thirsk and York (not every day). There are mainline train connections from York and Middlesborough. We are always happy to provide advice on the best way to get to the start of your holiday.

SALTBURN (East Section): Saltburn has a railway station with connections to the mainline network via Middlesborough.

RETURN from FILEY: There is a regular bus service between Filey and Scarborough, where there are train connections to the mainline rail network.

Book this Holiday

Cleveland Way map
The Cleveland Way is a reasonably challenging walk with a fair amount of ascent and descent. Over its approximately 110 miles, you will encounter a variety of underfoot conditions and will find yourself in some remote (and beautiful) locations. However, it is not all moors and cliff tops and there are stretches of woodland trails and interesting sights along the way such as the Norman abbeys of Rievalaulx and Whitby, the attractive fishing villages of Staithes and Robin Hoods Bay, and the seaside resorts of Saltburn, Scarborough and Filey.