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Walking the Cleveland Way - United Kingdom
Find your perfect trip!
Find your perfect trip!
The Cleveland Way walking
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Level :
Duration :
12 days
Comfort :
Apr May Jun Jul Aug Sep Oct
price in double room from: € 1.360
The Cleveland Way walking

The Cleveland Way walking

177 km from Helmsley to Filey

  • Combination of moorland, farmland, forest and coastal walking
  • Much historical interest
  • Robin Hood’s Bay with its cliff-hangning cottages
  • Remains of Norman Rievaulx Abbey & 13th C Whitby Abbey
  • Possibly the most beautiful view of the Yorkshire coast
  • Complete a real challenge on foot, without things being too challenging
UKSWWCX - The Cleveland Way walking
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Start: Helmsley       Finish: Filey

Day 1: Arrival in Helmsley
Day 2: Helmsley to Sutton Bank (18km / 11 mi)
Day 3: Sutton Bank to Osmotherley (18,5km / 11,5 mi)
Day 4: Osmotherley to Clay Bank Top (21km / 13 mi)
Day 5: Clay Bank Top to Great Ayton (15km / 9,5 mi)
Day 6: Great Ayton to Saltburn (23,8km / 15 mi)
Day 7: Saltburn to Runswick Bay (19km / 12 mi)
Day 8: Runswick Bay to Whitby (13,5km / 8,5 mi)
Day 9: Whitby to Robin Hood's Bay (11km / 7 mi)
Day 10: Robin Hood's Bay to Scarborough (24km / 15 mi)
Day 11: Scarborough to Filey (17km / 10,5 mi)
Day 12: End of programme

Day 1:    Arrival in Helmsley

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 nice pubs, cafes and shops to browse and visit.

Day 2:    Helmsley to Sutton Bank (18km / 11 mi)

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.

Day 3:    Sutton Bank to Osmotherley (18,5km / 11,5 mi)

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.

Day 4:    Osmotherley to Clay Bank Top (21km / 13 mi)

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 down the hill to Great Broughton.

*Overnight in Great Brougthon

Day 5:    Clay Bank Top to Great Ayton (15km / 9,5 mi)

Your host transfers you 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.

Day 6:    Great Ayton to Saltburn (23,8km / 15 mi)

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.

Day 7:    Saltburn to Runswick Bay (19km / 12 mi)

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!

Day 8:    Runswick Bay to Whitby (13,5km / 8,5 mi)

Quite a short day giving you the chance to have a good look round Whitby.

From Runswick, there is another section of cliffs before reaching Sandsend, from where you walk along above the beach into Whitby. This red-roofed town grew rich especially between 1750 and 1850 on fishing, whaling, 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 'n' chips meal here!

Day 9:    Whitby to Robin Hood's Bay (11km / 7 mi)

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's 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.

Day 10:    Robin Hood's Bay to Scarborough (24km / 15 mi)

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.

Day 11:    Scarborough to Filey (17km / 10,5 mi)

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.

Day 12:    End of programme

Arrangements end after breakfast.

Carlton Lodge (Helmsley)
Carlton Lodge (Helmsley)

Carlton Lodge is a fine country inn and formed of two buildings, which are local landmarks. It is renowned throughout the area for its culinary delights and fine selection of wine and beers.

Boltby & Kilburn
Boltby & Kilburn

We use a couple of nice B&Bs in the nearby villages of Boltby and Kilburn. Alternatively your host in Helmsley will pick you up from Sutton Bank and you will return to Helmsley for the night (included in cost).

The Golden Lion (Osmotherley)
The Golden Lion (Osmotherley)

The Golden Lion is a lovely friendly inn in the middle of the village. A warm welcome and very nice ensuite rooms await.


Wainstones Hotel (Great Broughton)
Wainstones Hotel (Great Broughton)

This present day structure has developed around a former dwelling dating from early 1700.


Royal Oak Hotel (Great Ayton)
Royal Oak Hotel (Great Ayton)

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.


The Victoria Guesthouse (Saltburn)
The Victoria Guesthouse (Saltburn)

The Victoria Guesthouse is a family run guesthouse situated only a few hundred yards from the beach.

The Firs Guesthouse (Runswick Bay)
The Firs Guesthouse (Runswick Bay)

The Firs guesthouse is a large detached stone built family run guesthouse.


Saxonville Hotel (Whitby)
Saxonville Hotel (Whitby)

Well situated on Whitby’s West Cliff, the comfort and hospitality of this hotel can be found just a few minutes stroll from the narrow streets and winding alleyways of this delightful, historic town.


The Villa Guesthouse (Robin Hood's Bay)
The Villa Guesthouse (Robin Hood's Bay)

The Villa Guesthouse is is elegantly refurbished Victorian guesthouse with many original features.


This program can be booked any day between Late March and mid-October, subject to availability. 

The nearest international aiports to fly to are Leeds (Bradford), Newcastle (Teeside), London aiports

Getting to Helmsley

The best way of getting to Helmsley is by bus from York, which is 2hrs by train from London / 1hr by train from Newcastle, 20mins by train from Malton. The bus then from York to Helsmley is 30 mins. 

Return from Filey

At the end of the tour, most people will probably want to take the train from Filey to Scarborough to link into train services to York, then elsewhere. 

If you have to return to Helmsley to pick up your car: there are several daily buses from Filey.


GPS tracks are available on request.



  • 11 nights' accommodation (small hotels, guesthouses, and inns)
  • 11 breakfasts
  • One piece of luggage per person transferred between accommodations, not exceeding 20kg
  • Detailed route descriptions (digital and printed at 1st accommodation)
  • 24-hour telephone assistance
  • Routes in digital format (.gpx) for GPS or mobile devices

Not included

  • Dinner, lunch and drinks
  • Travel to the start and from the end point of the trip
  • Admission fees
  • Personal expenses such as laundry and phone calls
  • Unscheduled transfers required during the trip


  • Single room supplement(s)
  • Solo traveller supplement
  • Airport transfers
  • Extra nights


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