Cleveland Way
Highlights:
Expanses of heather moorland
Sutton Bank escarpment vistas
Sea cliffs and rugged cliff paths
Smuggling coves; fishing villages
Brief:
⏱ Duration: 9 Days
🗺 Distance: 176 km
⛰ Difficulty: Moderate
🗓 Best Time: March - Nov
🛏 Accomm: B&B; hotels
Walk Overview
The Cleveland Way is one of the UK’s sixteen specially protected ‘National Trails’. It’s the second oldest of the National Trails and turned 50 in 2019. Like a faithful long-term friend, it’s cherished by those that know it.
The Cleveland Way is particularly feted for its diversity - starting high up on the lonely North York moors and tracing a line north-east around the edge of the North York Moors National Park till it reaches the coast, from where it heads south revelling in high cliffs, narrow coves and quaint fishing villages.
The Cleveland Way runs between Helmsley, in the south-west corner of the North York Moors National Park, and Filey on the North Sea coast. The trail takes a horseshoe shaped route between the two. You can walk the Way in either direction, although most people start in Helmsley probably because finishing at an attractive seaside resort has an appeal. There’s an additional practical reason for starting in Helmsley which is that the luggage transfer firms prefer that.
It’s certainly a walk of two halves. The half from Helmsley to Saltburn (92 kilometres) provides classic moorland scenery and expansive views from the edge of the escarpment that forms the western border of the North York Moors. The author James Herriott described the view from the escarpment at Sutton Bank as the finest vista in England. This half also delivers charming towns and villages, including, in particular, the starting town of Helmsley (worth spending a day there before beginning the walk) and the overnight villages of Osmotherley and Kildale.
The second half, from Saltburn to Filey (84 kilometres), is entirely on the coastline. This stretch of coastline has been designated a Heritage Coast and the bulk of it lies within the North York Moors National Park. It’s not hard to see why it’s so treasured. The trail takes in cliff-tops, with spectacular views both offshore and inland, and dips, curves and rises through coves and gulches. Along the way, the trail visits a number of attractive, historic towns and villages, including Staithes, Whitby and Robin Hood’s Bay.
The Cleveland Way provides several opportunities to visit areas associated with Captain James Cook. Before reaching the coast, on Easby Moor, the trail passes a large obelisk monument to the explorer. The monument is located near to his birth town of Great Ayton. Then, on the coast, Staithes and Whitby are places closely associated with Cook and are the sites of museums and monuments.
The Cleveland Way officially ends at Filey Brig, a stark promontory jutting into the North Sea. Filey Brig is a short walk from the town of Filey, a former fishing village that is now a popular beach resort with good transport connections.
The complete walk covers 176 kilometres (109 miles) and, at a good rate, generally takes about nine days of walking. Your total trip duration then depends on whether you incorporate rest days into the walk and, if so, how many.
Assistance and further information:
For assistance in undertaking the Cleveland Way, click the button below:
For more information on walking on the North York Moors, click the button below:
A nine day itinerary for walking the Cleveland Way is described below.
Itinerary
The walk takes about 9 days to complete. A typical 9 day itinerary is shown below.
Day 1
Helmsley to Sutton Bank
Distance: 17 km
Time: 5 hours
Accommodation: Bed & Breakfast
Day 2
Sutton Bank to Osmotherley
Distance: 18.5 km
Time: 5.5 hours
Accommodation: Bed & Breakfast
Day 3
Osmotherley to Clay Bank
Distance: 18 km
Time: 5.5 hours
Accommodation: Bed & Breakfast
Day 4
Clay Bank to Kildale
Distance: 15 km
Time: 4.5 hours
Accommodation: Bed & Breakfast
Day 5
Kildale to Saltburn-by-the-Sea
Distance: 24 km
Time: 7 hours
Accommodation: Bed & Breakfast; hotels
Day 6
Saltburn-by-the-Sea to Sandsend
Distance: 27 km
Time: 8 hours
Accommodation: Bed & Breakfast
Day 7
Sandsend to Robin Hood’s Bay
Distance: 16 km
Time: 4.5 hours
Accommodation: Bed & Breakfast
Day 8
Robin Hood’s Bay to Scarborough
Distance: 23.5 km
Time: 7 hours
Accommodation: Bed & Breakfast; hotels
Day 9
Scarborough to Filey
Distance: 18 km
Time: 5.5 hours
Accommodation: Bed & Breakfast; hotels
Walk Options
Guided
There are a limited number of tour operators offering part or all of the Cleveland Way as a guided trip. You can choose to do the entire 176 kilometres (109 miles) walk or opt for shorter versions. The tour operators that offer the full walk generally follow an itinerary along the lines of that described above.
Tour operators that offer guided trips generally operate on the basis of scheduled departure dates during the walking season.
Some guided tour operators offer accommodation at one central base (usually spacious and comfortable) and walkers are transferred to a section of the walk each day. Others utilise the available accommodation along the route, meaning the accommodation is more variable.
Typically, the package offered by the guided tour operators includes:
9 day tour with professional guides, 8 days of walking
8 nights accommodation
All meals
Transfers between the track and the accommodation (where applicable)
Assisted self-guided
A substantial number of tour operators offer the Cleveland Way as a self-guided trip.
Typically, the service includes:
Track notes, maps and information pack
Accommodation, usually with ensuites (the range and quantity of accommodation available in some villages is limited; also, the basic package offered by some tour operators might not always extend to ensuites)
Luggage transport between accommodation (and sometimes, where necessary, vehicle transfers between track and accommodation)
Breakfasts and optional packed lunches
24/7 Support
The duration of the self-guided options varies depending upon how far you wish to walk each day. Accommodation options range from comfortable through to luxury, again depending upon the size of the village or town and the purchased package.
Independent
There are camping grounds along the route that make camping on most nights a possibility. It’s also quite feasible to book accommodation along the route yourself and, if you require luggage transfers, to arrange that independently.
For those considering this option, it’s worth noting that the self-guided tour operators often have preferred rates with accommodation providers and luggage transfer companies. They also often have reserved allocations at the best-located/most suitable accommodation for the particular walk, so sometimes when accommodation shows no availability to an independent inquiry there’s still availability through a self-guided operator.
Also, be aware that the coastal stretch of the Cleveland Way is a popular destination for local holidaymakers, so during the holiday season it will usually be necessary to book accommodation well ahead of your visit.
Essential Information
Access
The starting point for the Cleveland Way is either Helmsley, North Yorkshire or Filey, North Yorkshire. Most people start in Helmsley.
Helmsley and Filey are both accessible by public transport:
There are regular trains between London’s Kings Cross Station and York;
From York to Helmsley, involves a train to Malton and then a bus or taxi from Malton to Helmsley (16 miles);
From Filey to York, there is a direct, frequent train service.
There are also buses between Scarborough and each of Helmsley and Filey. There are regular trains between Scarborough and London’s Kings Cross Station.
Best time
The best time to do the walk is between March and November.
Between June and August, with the heather in flower, the moorlands create a vast purple carpet. Sections of the coast can be busy in August.
Difficulty
The walk is rated at a difficulty level of moderate. It is waymarked and is generally well-defined and maintained.
Accommodation
There are many accommodation options at either end of the walk and, generally, plenty along the way. Accommodation options include camping, hostels, B&Bs, guesthouses, inns and hotels.
Many of the accommodation providers, particularly those near to the route, are attuned to walkers’ needs or offer amenities suited to walkers.
We can assist walkers in choosing the accommodation options which best suit their needs.
Dining
We can assist you in choosing some special dining options along the route.
Other activities
As a popular tourism destination, the North York Moors region offers many attractions in addition to the Cleveland Way.
Many walkers choose to add extra days to their trip so that they can explore these other attractions. Some walkers will do that through rest days along the trail; others prefer ‘add-ons’ at the end of the walk. Some do both!
Staithes, Whitby and Robin Hood’s Bay are all excellent places to spend extra time, as is Captain Cook’s birth town of Great Ayton and the walk’s starting point of Helmsley (with its historic market square and Helmsley Castle). The heritage town of York is also a wonderful place to visit.
We can assist walkers to explore the many attractions of the North York Moors.
Assistance
We can assist walkers with various aspects of their walking holidays.