Cleveland Way

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Cleveland Way
England, UK

The Cleveland Way is a National Trail that stretches 175 kilometres through the changing landscapes and scenery from Helmsley, on the southern edge of the North York Moors National Park, to Filey on the east coast.

Officially opened in 1969, it was the second official National Trail of England and Wales.

One of its main draws is the combination of heather moorland and coastal scenery that it offers.

This long-distance path follows a horseshoe, starting in the market town of Helmsley and arcing over the North York Moors National Park before reaching the coast at Saltburn.

From here the trail follows the dramatic North Yorkshire coastline to Filey, passing old fishing villages and lively coastal towns. Of all the walks in the UK, for sheer sustained glory, few could beat the Cleveland Way’s varied landscapes.

Some lengths of the Cleveland Way are bridleways or minor roads making them suitable for cycling or horse riding, but the entire route cannot be cycled as most of it is footpath.

  • Perfect combination of dramatic coastline and heather moorland with castles, ancient stone crosses and fishing villages en route.
  • Panoramas over the North York Moors.
  • Can be broken up into shorter or circular routes.
Walk Map
About the route
  • Travel

Getting to the start point in Helmsley is relatively easy with various options. If driving, Helmsley lies on the A170 and at the end of B1257 but bear in mind how you will get back to your car from Filey if you are walking the full trail.

If you wish to return to Helmsley at the end of your walk, it can be a difficult journey by public transport so it’s often worth organising a taxi or shuttle. If you’re on public transport then regular train services operate from Filey to London Kings Cross via Scarborough and York and North to Edinburgh on the East Coast mainline.

If you’re coming from further afield, the nearest International Airport is Leeds Bradford from which you can jump on a train to Malton and then bus to Helmsley. Trains run to Malton from other nearby hubs such as York.

  • Length

Most people complete the trail in a nine-day, one-way trip but it’s worth taking longer if you want to see some of the interesting places along the way.

Equally, it’s not necessary to complete the trail in one go to enjoy the best it has to offer.

There are a number of circular walks based on the Trail including one and two day walks, and shorter accessible walks for people of all abilities to enjoy.

  • Grade and difficulty of the walk

The route covers various terrains, encompassing rolling countryside and moorlands with a few steeper coast climbs, but luckily no mountains. For anyone that is a regular walker or has done some training it’s very achievable.

Underfoot the paths are generally well defined and maintained, but at times it can be rough with some muddy paths (particularly post-rain), so good footwear with ankle support is recommended.

Through the Moors section the climbs are generally longer and gentler but can be short and sometimes steep along the coast.

There are a series of easy access walks are suitable for people with impaired mobility or with a pushchair – just check out the National Trails website to find a suitable option.

  • Experience

As mentioned above, the Cleveland Way should be well within the capability of anyone who is reasonably fit and/or a regular walker.

A well-worn in pair of walking boots and a love for the countryside are about all you’ll need!

  • Permits

As with most National Trails, there is no need for a permit to complete some or all of this route, which means you can keep coming back time and time again.

  • Guided or self-guided

As with all National Trails, the route is way-marked along its length with the acorn symbol, along with coloured arrows that mark the status of each particular section. This means that the Cleveland Way can easily be done without a guide. This way you can also pick and choose when and where you stop.

Whilst the route is well signed at on stiles, gates and signposts throughout, an up-to-date map or GPS on your phone is highly recommended.

Navigating the trail is relatively straightforward, but year-round you may encounter hill fog or low cloud on the North York Moors, so you’ll need a map to fall back on. A guided tour takes the hassle out of booking accommodation and choosing how to break up the route.

An organised tour with accommodation, guide, maps and luggage transport will cost around £750.

best time to walk

The Cleveland Way can be walked year-round but winter weather is colder, boggier and more unpredictable.

The summer months are the busiest but also the most pleasant. If you want to see the moorland heather in bloom, then this takes place in late August and September.

Most people walk the route from Helmsley through to Filey in a clockwise direction so that the wind is behind them but really it can be walked in either direction. In peak season, walking it backwards and starting on a weekday might help with securing accommodation.

The below nine-day itinerary allows for covering comfortable daily distances and stops off in towns with various amenities.

Day 1:
Helmsley to Kilburn – 18km

Day 2:
Kilburn to Osmotherley – 21km

Day 3:
Osmotherley to Great Broughton – 18km

Day 4:
Great Broughton to Great Ayton – 19km

Day 5:
Great Ayton to Saltburn-By-The-Sea – 21km

Day 6:
Saltburn-By-The-Sea to Runswick Bay – 19km

Day 7:
Runswick Bay to Robin Hood’s Bay – 23km

Day 8:
Robin Hood’s Bay to Scarborough – 23km

Day 9:
Scarborough to Filey – 18km

The Cleveland Way also connects and intersects with various other long distance footpaths. These include the White Rose Walk, the North Sea Trail, the Esk Valley Walk and the Coast to Coast Walk.

For those looking to do a subsection, official circular walks along the Cleveland Way include Ravenscar Round,Great Ayton Try-a-Trail and Osmotherley and the Drovers Road.


Thanks to its course past various villages and towns, there is plenty of accommodation along the trail. Having said this, it does book up quickly in peak (summer) season so should be planned and booked as far in advance as possible.

As with most long-distance trails, there are several companies that can transport your luggage from one place to the next – these should also be booked ahead of time but save you lugging your kit with you.

There aren’t that many hostels or bunkhouses en route but there are numerous B&Bs and cheap pub rooms. If you plan to camp note that it is not technically legal to wild camp in England, even if some landowners are open to it, it’s better to stay on official campsites.

These are all listed out on the National Trail website and most offer good amenities.

What to do

Visitors are not only treated to amazing views along the way but also a wealth of history and heritage. Helmsley Castle, Rievaulx Abbey, Mount Grace Priory, Gisborough Priory, Whitby Abbey and Scarborough Castle are just some of the sites that are enjoyed as part of the trail.

Spending an extra day at one of the towns is not a bad idea either. Historic Whitby was the home of Captain Cook and offers up a stunning abbey and harbour whilst Staithes is arguably the prettiest village on the trail with amazing cobbled lanes, the infamous Cod and Lobster pub and the grocer where James Cook worked.

Filey, the finish point, is also an attractive seaside town with a magnificent beach, dramatic views of the long black finger of Filey Brigg in one direction and the chalk headland of Flamborough Head and Bempton Cliffs in the other.

Head to the RSPB Reserve at Bempton Cliffs and catch sight of up to 200,000 nesting birds including gannets, guillemots and kittiwakes during breeding season.

Going off the track, enjoy a secret picnic by the waterfall at Hayburn Wyke, a secluded cove between Scarborough and Whitby that is a hidden gem, or take a bike ride through beautiful woodland at Sutton Bank whilst gliders soar overhead.

Published: October 13, 2019 Modified: April 24, 2020
Mickledore specialises in self-guided walking holidays in the UK for the independent traveller.
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At a glance
Difficulty 2/5
Starts at North York Moors National Park, United Kingdom
Finishes at Filey, UK
Length of route 175 Km
Average time to complete 9 - Days
Possible to complete sub-sectionsYes
Highest point 452 metres
Permit requiredNo
Countries visited England, UK