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12 days
  • self guided walk
  • 11 nights in guesthouses and hotels
  • 11 Breakfasts





Trip Code: WCX

Trip highlights

  • Bracing Walking on North Yorkshire Trails
  • A Mix of Coastal and Moorland Walks
  • Much Historical Interest
  • Complete a Real Challenge, Without Things Being Too Challenging!

Walkers familiar with Wainwright’s Coast to Coast path will already be well acquainted with a couple of spots along the rolling Cleveland Way such as The Wainstones, Urra Moor and Robin Hood Bay. In fact it shares about 10 miles of routing with the ‘C to C’. Maybe they will be intrigued enough by their flirtation with the trail to don their boots once again and take up the challenge of the 110 mile Cleveland Way route from Helmsley to Filey in its entirety. What stands out is the experience of half a walk over hill and scarp edges and half along the hilly coastline of the Yorkshire seaside. There is much to enjoy for those interested in history, those ‘collecting’ National Trails and for aficionados who wish to enjoy arguably the best Fish ‘n’ Chips in England at Whitby Bay! This is the second of the ‘National Trails’, dating from 1969 and is rooted in the North York Moors National Park / Yorkshire Heritage Coast. Along its length there are contrasts in walking between field - quilted farmlands, forest patches, dramatic sandstone rock scarps, bleak moorlands and the highly eroded coastline, punctuated by beautiful little fishing villages, clinging to the cliffs. It is an area that has been threatened by the expansion of the Tyne – Tees Conurbation on the one side and by the encroaching North Sea on the other. However apart from busy coastal towns such as Scarborough, it remains a tranquil area, bolstered and protected by the presence of the National Park of which about 80% of the walk occupies. Highlights of the Cleveland Way include, the remains of the Norman Rievaulx Abbey, and 13th century Whitby Abbey (but dating from the 7th century!), the Captain Cook Monument and Robin Hoods Bay with it's cliff-hanging cottages. Most of the route follows well sign-posted footpaths, which generally have good surfaces and are easy to follow. The exception to this is along the coastal path, which, in some places, is overgrown and uneven underfoot. The amount of daily ascent and descent is moderate, with much of the walk being on level or gently sloping ground. There are a number of steep ascents along the section from Osmotherley to Urra Moor and at some places along the coast, but these are generally of no more than one or two hundred metres at a time.

Trip Grading


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Make your own way to Helmsley and settle into this attractive old market town. Visit the ruins of the castle keep with echoes of the English Civil War in 1644. There are a couple of nice pubs to visit. Accommodation: The Black Swan is a wonderful pub dating back to the 15th century. With an Elizabethan building on one end, a Tudor one to the other and a Georgian House in the middle, the Black Swan is wonderfully higgledly-piggledy, with bags of character.

Meals:  Nil

After breakfast depart Helmsley on this easy section across the wooded Rye Valley, then ascend gently up to the Tabular Hills and onto the great viewpoint at Sutton Bank, with views to a Victorian chalk horse carved into the hillside. Enroute you can visit the famous 12th century Rievaulx Abbey. A transfer has been arranged to pick you up from Sutton Bank and you will return to Helmsley for the night (included in cost).

Meals:  B

After breakfast, you will be transferred back at Sutton Bank. Today is more or less level walking along the escarpment of the Hambleton Hills with views over the vale of York. The walk follows the ancient Hambleton Cattle Drovers Road to the old market and mining village of Osmotherley with the remodeled 15th century church with 12th century Scandinavian carvings. Accommodation: Vane House is a large old stone guesthouse. A friendly welcome is offered and all spacious rooms are ensuite.

Meals:  B

After the warm up of the last couple of days, hopefully you are ready to enjoy what most people would claim to be the hardest day of the route, as you are ascending and descending over a succession of moors to Clay Bank Top. The views in reasonable weather are extensive. The Coast-to-Coast shares this day and it is a roller coaster ride of a walk up and down beside the crags of Cringle Moor and the famous Wainstones. We come off the ridge at Clay Bank Top and you will get a transfer to your accommodation (included) from the car park at Clay Bank Top to Great Broughton. Accommodation: Great Broughton - Wainstones Hotel, this present day structure has developed around a former dwelling dating from early 1700.

Meals:  B

Transfer back to Clay Bank car park and then you start the day with a steep ascent up onto Urra Moor and the highest point of the journey at Round Hill 454m. You are now walking on exposed high moorland, following the line of the disused Ironstone railway line and drovers roads, with many ancient features, such as boundary stones, tumuli and cock pits before descending to cross the remote hamlet and railway station at Kildale. Ascend again, passing the Captain Cook memorial. Accommodation: Royal Oak Hotel this 18th century rural hostelry is at the heart of the village. Original features include the beamed ceilings and welcoming log fires, which add to the charm and character of this traditional inn.

Meals:  B

The walk continues through forests with a diversion to “Rosberry Topping” an outlying craggy hill. It is a steep climb, but the views on a clear day are outstanding. The trail follows more moorlands and then through the Guisborough woods and steeply down to Slapewath, an area of old mineral workings. Perhaps fortify yourself with a pint before continuing the last 7 km/ 4.5 miles to Saltburn-by-the-Sea; an old fishing village; come small Victorian seaside resort that was once famed for salt making and smuggling! The whole nature of the walk changes from here as you head off along the coast. Accommodation: The Victoria Guesthouse is a family run guesthouse is situated only a few hundred yards from the beach.

Meals:  B

Walk along successive dramatic cliffs, past the highest point on the English east coast at “Rock Cliff” near Boulby. Highlight of the walk today is the beautiful little fishing village of Staithes. The fishing boats at the quay are called Cobles and they still set out to undertake this dangerous activity. Captain Cook served his apprenticeship in a shop on the seafront which has long ago, been stolen by the sea! The trail continues onto the red roofed attractive village of Runswick Bay, by the Jurassic shale cliffs, a fossil hunter’s paradise! It is difficult to secure 1 night stays in Runswick Bay so we will book a 2 night stay in Whitby. You can easily move between Runswick Bay & Whitby on the bus (own expense) or alternatively we would be happy to organise a return taxi transfer for you (own expense). Accommodation: Chiltern Guesthouse is a small seaside BB situated close to the harbour and beach. Of course this is a busy town and alternative accommodation will be used.

Meals:  B

Start your day with a short bus ride back to Runswick Bay (own expense). Quite a short day giving you the chance to have a good look round Whitby Bay. From Runswick, there is another section of cliffs before reaching Sandsend, from where you walk along above the beach to Whitby Bay. This red roofed town grew rich especially between 1750 and 1850 on fishing, whaling, jet mining and shipbuilding. Whitby is also famous for its Abbey ruins and for Count Dracula (there is a Dracula Trail in the town). We would recommend that of all the places on this route, you have a fish meal here!

Meals:  B

The shortest day, giving you the opportunity for a leisurely breakfast and late start. The climb out of Whitby Bay involves 199 steps and takes you up to the old abbey ruins, and to St Mary’s church with its boat deck construction inside. The trail then follows the coastal cliffs once more, with good bird life, depending on the time of year! You then rejoin the Coast-to-Coast trail for the last few miles into Robin Hood Bay. This little places drops steeply down to the sea and the Bay Hotel is a good place to sit with a beer on the ocean terrace, watching the sea and all those people celebrating that have just completed the Coast to Coast walk. Accommodation: The Villa Guesthouse is is elegantly refurbished Victorian guesthouse with many original features.

Meals:  B

After a couple of easy days, you now have quite a long one to the seaside resort of Scarborough, certainly the largest settlement that you will visit on this tour! The route goes past the planned for but abandoned resort of Ravenscar where the Victorian street layouts can be detected where the grass has receded. At nearly 200 metres high, you will get possibly the most beautiful view of the Yorkshire coast. You then follow the cliffs gradually descending into Scarborough with its two sandy bays, castle remains on a headland and chances for swimming, ice cream etc. This is said to be the first English seaside resort, having long been associated with spring waters from the 1600s. Accommodation: We use a number of guesthouses in this busy seaside town.

Meals:  B

The last stretch of your walks meanders along behind Cayton Sands and then along the cliffs again to the calcareous grit stone promontory at Filey Brigg (also a nature reserve). If it is low tide, you can cross the sands to finish at Filey, otherwise you need to retrace your steps to get round to this pleasant fishing/resort town. Accommodation: Rutlands West Guesthouse is a beautifully refurbished Edwardian B&B, it is well situated between the town & beach.

Meals:  B

Depart Filey after breakfast.

Meals:  B



The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.
On self guided trips, actual route information provided before departure will be more detailed.


  • 11 breakfasts
  • 11 nights accommodation in guesthouses and hotels on a twin share basis with ensuite facilities where available
  • One piece of luggage per person transferred from Inn to Inn, not exceeding 18kg
  • Information pack including route notes & maps (1 pack per room booked)
  • Emergency hotline
  • Return transfer Helmsley/Sutton Bank
  • Return transfer Clay Bank Top/Great Broughton
  • GPX Files

  • Lunch, Dinner and drinks
  • Entrance fees
  • Travel insurance
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls
  • Unscheduled transfers required during the trip
  • Cost of bus between Runswick Bay & Whitby return
  • A supplement will apply if you are travelling solo or book a single room
  • Guide - this is a self guided holiday
  • Excess Luggage




Not particularly long days but some steep climbs and descents. Generally, however undulating. Mixed weather can be expected. We would not recommend the route for first time walkers.

Departure dates

Daily from 31 Mar to 05 Oct


High Season
Please note that minor changes to your 2024 itinerary may apply.

Want to organise a private group?

Fundraising events, sporting groups, family treats; learn how you can organise a Private Group from just 6 travellers.

Priceper person from


Options & Supplements*
  • Single Supplement 2024USD$620
  • Solo Traveller Supplement 2024USD$660
  • Single Supplement 2025USD$680
  • Solo Traveller Supplement 2025USD$680
*Prices listed are per person

Frequently Asked Questions

Yes it is an English National trail and is generally well waymarkesd with the white acorn mark

Yes, the day between Osmotherley and Clay Bank top and also about 3 miles along the coast just before Robin Hood's Bay

Because of limited accommodation at these places and hence you get two nights in Helmsley and a night off route below Claybank Top and two nights at Whitby

You will find day walkers, dog walkers and people on the Coast to Coast parts of the path. you won't see that many people who are walking the whole route

It contains one of the largest expanses of heather moorland in England and Wales covering an area of over 44,000 hectares or around one third of the National Park. The North York Moors is a European Special Protection Area for merlin and golden plover and is internationally renowned as a haven for ground nesting birds.

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The Cleveland Way

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