Cleveland Way Self Guided Holiday | Load off Your Back
Walk the Cleveland Way
Majesty, History and Drama
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About the Trail:

The first section of the Cleveland way provides an easy walk across the richly wooded landscape of the Rye Valley, and then rises gently to the flat limestone of the Tabular Hills. The end of this section provides spectacular panoramic views from the escarpment edge between the White Horse and Sutton Bank. Leaving Sutton Bank, the trail carries on Gormine Lake. This relic of the Ice Age is the only natural lake on the North York Moors. This lake opens onto the idyllic setting of Oakdale’s reservoirs. From thereon in, the walk follows the coastline, with amazing sea views and imposingly rugged cliff faces. Once it reaches Saltburn, the path takes you up along a section of dramatic cliffs to the highest point on the East Coast of England at Rock Cliff near Boulby, and carries on through many picturesque fishing villages, eventually reaching the historic towns of Scarborough and Filey, which mark the end of the trail.

Highlights: The path passes a multitude of English Heritage sites; keep an eye out for Whitby Abbey, rendered famous in Bram Stoker’s 1897 novel Dracula, and further used in the film adaptation of the same name. Other sites to visit are Rievalux Abbey, one of the wealthiest abbeys in England until is dissolution by Henry VIII in 1538, and Scarborough Castle, a former medieval Royal fortress which was fortified and defended through numerous civil wars, invasions, sieges and conflicts.

The nature of the Trail:

There are some steeper sections along this walk, particularly towards the coast. The cliffs are steep and can occasionally be subject to slumping, and in wet weather the paths can become slippery. Caution is advised on this section of the route in wet weather. Aside from this, the route is clearly signposted and easy to follow, with no particular extremes of conditions or weather throughout the route.

You might also be interested in the Ravenscar - Yorkshire's North Coast organised group holiday as part of our Ramblers Walking Holidays programme.

Hemsley to Saltburn-by-the-Sea - 5 Days

5 days walking
6 nights accommodation
55 miles /88.5km
From:
£410  Per Person
Single Supplement:
£20 Per Person Per Night
Solo Traveller Supplement:
£30  Per Person Per Night
Season:
spring, summer, autumn

Itinerary

Arrival - Arrival and overnight stay in the Helmsley area
Helmsley a picturesque Yorkshire town with plenty of cafes, shops and restaurants. Places to visit include Helmsley Castle, a medieval fortress turned Tudor mansion with a wealth of history to explore, and Helmsley Walled Garden, a five acre stretch of restored garden nestled at the foot of the North York Moors. There is easy access to the public transport with connections to York, Malton, Thirsk, Middlesbrough, Great Ayton, Whitby, Scarborough and Filey.

Day 1 - Helmsley to Sutton Bank (10½ miles / 17 km)
Walk through woodlands and along Rye Valley towards the ruins of 12th century Rievaulx Abbey, one of the wealthiest abbeys in England until it was dissolved by Henry VIII in 1538. You'll then follow a forestry track with beautiful views of Hambleton Hills and the edge of Roulston Scar, an iron age hillfort built around 400 BC.

3 hours walking. Highest point (Casten Dyle): 294m (965ft)

Day 2 - Sutton Bank to Osmotherly (11½ miles / 18½ km)
A high level walk over the Sutton Bank escarpment. The trail stays close to the edge of Hambleton Hills most of the time and passes an ancient road used in 18th and 19th centuries before reaching Osmotherly, a village at the western edge of the North York Moors.

5 hours walking. Highest point (Black Hambleton): 387m (1,269ft)

Day 3 - Osmotherly to Clay Bank (11 miles / 17½ km)
This section crosses over five moors (Scarth Wood Moor, Live Moor, Cringle Moor, Cold Moor and Hasty Bank) and offers fantasic vistas of the surrounding countryside, finishing in Hasty Bank. A beautiful route surrounded by woodlands with expansive views of all 110 miles of the Cleveland Hills.

7 hours walking. Highest point (Cringle Moor): 404m (1,327ft)

Day 4 - Clay Bank Top to Gribdale Gate (7½ miles / 12 km)
Walk through moorlands with views of the highest point on the North York Moors trail: Round Hill and the surrounding Urra Moor, well known for its prehistoric remains. The path then follows an ancient road towards Gribdale Gate.

3 hours walking. Highest point (Round Hill): 455m (1,489ft)

Day 5 - Gribdale Gate to Saltburn-by-the-Sea (14½ miles (23frac12; km)
The trail heads towards Roseberry Topping, then descends Cockshaw Hill and leads you to Newton then covers forest tracks before entering Skelton. Saltburn-by-the Sea has its own station serviced by Northern Rail from where you can get direct trains to Middlesbrough, Darlington, and Bishop Auckland.

5 hours walking. Highest point (Easby Moor): 323m (1,060ft)

Departure - Departure from Saltburn-by-the-Sea
Your holiday arrangements end after breakfast

Notes

Please be aware that slight variations to these itineraries may have to be made due to availability of accommodation. Please note that the quoted daily mileage does not include distance from the path to your overnight accommodation.

Our prices are based on two persons sharing a room. If you are travelling with others and require your own room, the single price applies.

If you are walking the route by yourself, the Solo Traveller price applies If you wish to add rest days into the itinerary please contact us for details.

Saltburn-by-the-Sea to Filey - 5 Days

5 days walking
6 nights accommodation
54 miles /87km
From:
£415  Per Person
Single Supplement:
£20 Per Person Per Night
Solo Traveller Supplement:
£30  Per Person Per Night
Season:
spring, summer, autumn

Itinerary

Arrival - Arrival and overnight stay in Saltburn-by-the-Sea area
Saltburn-by-the-Sea is a Victorian sea side resort. You might like to visit its Italian Gardens, an Italian-style public park designed by Robert Everatt in 1860, Saltburn Miniature Railway, opened in 1947 and still running to this day, and Saltburn Pier, the most northerly pleasure pier in Britain. There are good public transport connections to national rail services and buses.
Day 1 - Saltburn-by-the-Sea to Staithes (9 miles / 14½ km)
Walk through sections of hills up to Rock Cliff near Boulby, an old mining village, and from there the path continues along an old railway track that used to service the Boulby mine. The path then carries on along the beach towards Staithes, an improbably attractive old fishing town, famous for the fossils found in the cliffs surrounding the village which was also home to Captain Cook.
Day 2 - Staithes to Whitby (11½ miles / 18½ km)
The rrack continues along the beaches of Runswick Bay and Sandsend with some cliff top walking, offering wonderful views out over the coast. Take care and keep a safe distance from the cliff edge.
Day 3 - Whitby to Robin Hood’s Bay (7 miles / 11 km)
The route climbs gently uphill and follows the cliff edge into Whitby with spectacular views of Coastal scenery, passing by the old lighthouses and radar stations of the 2nd World War. Places to visit include Whitby Abbey, a Benedictine abbey established in the year 657 AD, and the Robin Hood’s Bay museum, containing a variety of artefacts documenting local history.
Day 4 - Robin Hood’s Bay to Scarborough (14½ miles / 23 km)
This section offers plenty of cliff top walking with sudden drops to sea level. The route continues onto a beautiful wooded section of the path, which offers flat and easy walking. The route ends in Scarborough, the largest holiday resort on the Yorkshire coast and draws tourists from around the world.
Day 5 - Scarborough to Filey (12 miles / 19 km)
From Scarborough’s South Cliffs, the path continues along the hillside for the rest of the trail with some fine views of the coast. There are train connections which run to and from Filey and a regular bus service operating through main villages on the Cleveland Way.
Departure - Departure from Filey after breakfast
Your holidays arrangements end after breakfast

Notes

Please be aware that slight variations to these itineraries may have to be made due to availability of accommodation. Please note that the quoted daily mileage does not include distance from the path to your overnight accommodation.

Our prices are based on two persons sharing a room. If you are travelling with others and require your own room, the single price applies.

If you are walking the route by yourself, the Solo Traveller price applies If you wish to add rest days into the itinerary please contact us for details.

Helmsley to Filey - 7 Days

7 days walking
8 nights accommodation
110.5 miles /178km
From:
£540  Per Person
Single Supplement:
£20 Per Person Per Night
Solo Traveller Supplement:
£30  Per Person Per Night
Season:
spring, summer, autumn

Itinerary

Arrival - Arrival and overnight stay in Helmsley area
Day 1 - Helmsley to Osmotherly (21½ miles / 34½ km)
Walk through woodlands and along Rye Valley towards the ruins of 12th century Rievaulx Abbey, one of the wealthiest abbeys in England until it was dissolved by Henry VIII in 1538. You'll then follow a forestry track with beautiful views of Hambleton Hills and the edge of Roulston Scar, an iron age hillfort built around 400 BC. The trail stays close to the edge of Hambleton Hills most of the time and passes an ancient road used in 18th and 19th centuries before reaching Osmotherly, a village at the western edge of the North York Moors.
Day 2 - Osmotherly to Clay Bank Top (11 miles / 17½ km)
This section crosses over five moors and offers fantasic vistas of the surrounding countryside, finishing in Hasty Bank with the highest point at Cringle Moor 1,327ft (404m). A beautiful route surrounded by woodlands with expansive views of all 110 miles of the Cleveland Hills.
Day 3 - Clay Bank Top to Roseberry Topping (13½ miles / 21½ km)
Walk through moorlands with views of the highest point on the North York Moors trail: Round Hill (1,489ft (455m) and the surrounding Urra Moor, well known for its prehistoric remains. The path then follows an ancient road towards Gribdale Gate.
Day 4 - Roseberry Topping to Staithes (19½ miles / 31½ km)
The path continues through Newton Moor to forest terrain at first before following a stone walled path. The route then leads you uphill towards Highcliff Wood, with excellent views of Guisborough and the coast beyond it. The last section passes forest terrain downhill, and the trail circles outside of a field following the route towards Skelton and Staithes, an improbably attractive old fishing town famous for the fossils found in the cliffs surrounding the village which was also home to Captain Cook.
Day 5 - Staithes to Robin Hood’s Bay (18½ miles / 29½ km)
Walk along the beaches of Runswick Bay and Sandsend with some cliff top walking and fine views of Coastal scenery. The route climbs gently uphill follows the cliff edge into Whitby and Robin Hood’s Bay.
Day 6 - Robin Hood’s Bay to Scarborough (14½ miles / 23 km)
This section offers plenty of cliff top walking with sudden drops to the sea level. The route continues onto a beautiful wooded section of the path, which offers flat and easy walking. The route ends in Scarborough, the largest holiday resort on the Yorkshire coast and draws tourists from around the world.
Day 7 - Scarborough to Filey (12 miles / 19 km)
From Scarborough’s South Cliffs, the path continues along the hillside for the rest of the trail with some fine views of the coast. There are train connections which run to and from Filey and a regular bus service operating through main villages on the Cleveland Way.
Departure - Departure from Filey after breakfast
Your holiday arrangements end after breakfast

Notes

Please be aware that slight variations to these itineraries may have to be made due to availability of accommodation. Please note that the quoted daily mileage does not include distance from the path to your overnight accommodation.

Our prices are based on two persons sharing a room. If you are travelling with others and require your own room, the single price applies.

If you are walking the route by yourself, the Solo Traveller price applies If you wish to add rest days into the itinerary please contact us for details.

Helmsley to Filey - 9 Days

9 days walking
10 nights accommodation
110.5 miles /178km
From:
£680  Per Person
Single Supplement:
£20 Per Person Per Night
Solo Traveller Supplement:
£30  Per Person Per Night
Season:
spring, summer, autumn

Itinerary

Arrival - Arrival and overnight stay in Helmsley area
Helmsley is a picturesque Yorkshire town with plenty of cafés, shops and restaurants. Places to visit include Helmsley Castle, a medieval fortress turned Tudor mansion with a wealth of history to explore, and Helmsley Walled Garden, a five acre stretch of restored garden nestled at the foot of the North York Moors. Easy access to the public transport with connections to York, Malton, Thirsk, Middlesbrough, Great Ayton, Whitby, Scarborough and Filey. Bus service operates from York, Malton or Scarborough.
Day 1 - Helmsley to Sutton Bank (10 miles / 16 km)
Walk through woodlands and along Rye Valley towards the ruins of 12th century Rievaulx Abbey, one of the wealthiest abbeys in England until it was dissolved by Henry VIII in 1538. You'll then follow a forestry track with beautiful views of Hambleton Hills and the edge of Roulston Scar, an iron age hillfort built around 400 BC.
Day 2 - Sutton Bank to Osmotherly (11½ miles / 18½ km)
The trail stays close to the edge of Hambleton Hills most of the time and passes an ancient road used in 18th and 19th century before reaching Osmotherly, a village at the western edge of the North York Moors.
Day 3 - Oshmotherly to Clay Bank Top (11 miles / 17½ km)
This section crosses over five moors and offers fantastic vistas of the surrounding countryside, finishing in Hasty Bank with the highest point at Cringle Moor 1,327ft (404m). A beautiful route surrounded by woodlands with expansive views of all 110 miles of the Cleveland Hills.
Day 4 - Clay Bank Top to Gribdale Gate (7½ miles / 12 km)
Walk through moorlands with views of the highest point on the North York Moors trail: Round Hill (1,489ft (455m) and the surrounding Urra Moor, well known for its prehistoric remains. The path then follows an ancient road towards Gribdale Gate.
Day 5 - Gribdale Gate to Saltburn-by-the-Sea (15 miles / 24 km)
Trail follows the route towards Roseberry Topping, then descends Cockshaw Hill and leads you to Newton. Second part of the trail covers forest tracks before entering Skelton. Saltburn-by-the-Sea is a Victorian sea side resort. You might like to visit its Italian Gardens, an Italian-style public park designed by Robert Everatt in 1860, Saltburn Miniature Railway, opened in 1947 and still running to this day, and Saltburn Pier, the most northerly pleasure pier in Britain.
Day 6 - Saltburn-by-the-Sea to Runswick Bay (12½ miles / 20 km)
Walk through sections of hills up to Rock Cliff near Boulby, an old mining village, and from there the path continues along an old railway track that used to service the Boulby mine. The path then carries on along the beach towards Staithes, an improbably attractive old fishing town famous for the fossils found in the cliffs surrounding the village which was also home to Captain Cook. The track continues along the beaches of Runswick Bay with some cliff top walking, offering wonderful views out over the coast. Take care and keep a distance from the cliff edge.
Day 7 - Runswick Bay to Robin Hood’s Bay (15 miles / 24 km)
The route climbs gently uphill and follows the cliff edge into Whitby with spectacular views of Coastal scenery, and passing by the old lighthouses and radar stations of the 2nd World War. Places to visit include Whitby Abbey, a Benedictine abbey established in the year 657 AD, and the Robin Hood’s Bay museum, containing a variety of artefacts documenting local history.
Day 8 - Robin Hood’s Bay to Scarborough (14½ miles / 23 km)
This section offers plenty of cliff top walking with sudden drops to sea level. The route continues onto a beautiful wooded section of the path, which offers flat and easy walking. The route ends in Scarborough, the largest holiday resort on the Yorkshire coast and draws tourists from around the world.
Day 9 - Scarborough to Filey (12 miles / 19km)
From Scarborough’s South Cliffs, the path continues along the hillside for the rest of the trail with some fine views of the coast. There are train connections which run to and from Filey and a regular bus service operating through main villages on the Cleveland Way.
Departure - Departure from Filey after breakfast
Your holiday arrangements end after breakfast

Notes

Please be aware that slight variations to these itineraries may have to be made due to availability of accommodation. Please note that the quoted daily mileage does not include distance from the path to your overnight accommodation.

Our prices are based on two persons sharing a room. If you are travelling with others and require your own room, the single price applies.

If you are walking the route by yourself, the Solo Traveller price applies If you wish to add rest days into the itinerary please contact us for details.

Helmsley to Filey - 10 Days

10 days walking
11 nights accommodation
110.5 miles /178km
From:
£750  Per Person
Single Supplement:
£20 Per Person Per Night
Solo Traveller Supplement:
£30  Per Person Per Night
Season:
spring, summer, autumn

Itinerary

Arrival - Arrival and overnight stay in Helmsley area
Helmsley is a picturesque Yorkshire town with plenty of cafés, shops and restaurants. Places to visit include Helmsley Castle, a medieval fortress turned Tudor mansion with a wealth of history to explore, and Helmsley Walled Garden, a five acre stretch of restored garden nestled at the foot of the North York Moors. Easy access to the public transport with connections to York, Malton, Thirsk, Middlesbrough, Great Ayton, Whitby, Scarborough and Filey. Bus service operates from York, Malton or Scarborough.
Day 1 - Helmsley to Sutton Bank (10 miles / 16 km)
Walk through woodlands and along Rye Valley towards the ruins of 12th century Rievaulx Abbey, one of the wealthiest abbeys in England until it was dissolved by Henry VIII in 1538. You'll then follow a forestry track with beautiful views of Hambleton Hills and the edge of Roulston Scar, an iron age hillfort built around 400 BC.
Day 2 - Sutton Bank to Osmotherly (11½ miles / 18½ km)
The trail stays close to the edge of Hambleton Hills most of the time and passes an ancient road used in 18th and 19th centuries before reaching Osmotherly, a village at the western edge of the North York Moors.
Day 3 - Oshmotherly to Clay Bank Top (11 miles / 17½ km)
This section crosses over five moors and offers fantastic vistas of the surrounding countryside, finishing in Hasty Bank with the highest point at Cringle Moor 1,327ft (404m). A beautiful route surrounded by woodlands with expansive views of all 110 miles of the Cleveland Hills.
Day 4 - Clay Bank Top to Roseberry Topping (13½ miles / 21½ km)
Walk through moorlands with views of the highest point on the North York Moors trail: Round Hill (1,489ft (455m) and the surrounding Urra Moor, well known for its prehistoric remains. The path then follows an ancient road towards Gribdale Gate and approaches Roseberry Topping.
Day 5 - Roseberry Topping to Saltburn-by-the-Sea (10½ miles /17 km)
The trail descends Cockshaw Hill and leads you to Newton. Second part of the trail covers forest tracks before entering Skelton. Saltburn-by-the-Sea is a Victorian sea side resort. You might like to visit its Italian Gardens, an Italian-style public park designed by Robert Everatt in 1860, Saltburn Miniature Railway, opened in 1947 and still running to this day, and Saltburn Pier, the most northerly pleasure pier in Britain.
Day 6 - Saltburn-by-the-Sea to Staithes (9 miles / 14½ km)
Walk through sections of hills up to Rock Cliff near Boulby, an old mining village, and from there the path continues along an old railway track that used to service the Boulby mine. The path then carries on along the beach towards Staithes, an improbably attractive old fishing town famous for the fossils found in the cliffs surrounding the village which was also home to Captain Cook.
Day 7 - Staithes to Whitby 11½ miles / 18½ km)
The track continues along the beaches of Runswick Bay and Sandsend with some cliff top walking, offering wonderful views out over the coast. Take care and keep a distance from the cliff edge. Route climbs gently uphill and follows the cliff edge into Whitby with spectacular views of Coastal scenery.
Day 8 - Whitby to Robin Hood’s Bay (7 miles / 11 km)
Route climbs gently uphill and follows the cliff edge into Whitby with spectacular views of Coastal scenery, and passing by the old lighthouses and radar stations of the 2nd World War. Places to visit in Robin Hood’s Bay: Whitby Abbey, a Benedictine abbey established in the year 657AD, and the Robin Hood’s Bay museum, containing a variety of artefacts documenting local history.
Day 9 - Robin Hood’s Bay to Scarborough (14½ miles / 23 km)
This section offers plenty of cliff top walking with sudden drops to sea level. The route continues onto a beautiful wooded section of the path, which offers flat and easy walking. The route ends in Scarborough, the largest holiday resort on the Yorkshire coast and draws tourists from around the world.
Day 10 - Scarborough to Filey (12 miles / 19 km)
From Scarborough’s South Cliffs, the path continues along the hillside for the rest of the trail with some fine views of the coast. There are train connections which run to and from Filey and a regular bus service operating through main villages on the Cleveland Way.
Departure - Departure from Filey after breakfast
Your holiday arrangements end after breakfast

Notes

Please be aware that slight variations to these itineraries may have to be made due to availability of accommodation. Please note that the quoted daily mileage does not include distance from the path to your overnight accommodation.

Our prices are based on two persons sharing a room. If you are travelling with others and require your own room, the single price applies.

If you are walking the route by yourself, the Solo Traveller price applies If you wish to add rest days into the itinerary please contact us for details.

ACCOMMODATION ON THE ROUTE

Accommodation:

Depending on where you are on the trail you’re following, your overnight accommodation can vary from a B&B, guest house or hotel, which is all part of enjoying the countryside. Here are examples of the type of accommodation you can expect on The Cleveland Way. Wherever possible, we will reserve rooms with ensuite or private bathrooms. There may be locations or times of the year when accommodation with only shared facilities are available.

If you wish to add rest days into the itinerary please contact us for details.

How it Works


Included in the holiday arrangements and package cost:

  • Accommodation in B&Bs, guest houses, inns and small hotels on, or close by, the route
  • Breakfast daily
  • Daily baggage transfer - one bag per person up to 20kg (44lbs)
  • If you are booked off route for the evening, we will provide any necessary transportation between the route and your accommodation and back to the path again the next morning
  • A detailed map and/or guidebook of the long distance path chosen per room
  • Support and planning in implementing your trip
  • Information pack with full contact and location details on your overnight accommodation and baggage transfer company
  • Assistance of a 24/7 Duty Officer who will do everything to help you in case of an emergency.

  • Not included in the holiday arrangements and package cost:

  • Transportation to the start of your holiday or from the final night’s accommodation
  • Any parking costs for the duration of your holiday
  • Travel insurance
  • Lunches or dinners (or any travel costs in getting to nearby pubs or restaurants)

  • Arrival and Departure:

    Return transport back to your car at the end of the holiday is not included, however is often available by public transport or taxi.

    The nearest railway stations to the start of the trail (Helmsley) are in Malton and Scarborough. At the end of the trail there is a railway station at Filey which is linked by rail with London King's Cross. Rail timetables, fare and route information can be found at www.nationalrail.co.uk or by calling National Rail Enquiries on 03457 484 950.

    Coach travel information is available at www.nationalexpress.com or by calling National Express on 0871 781 8181

    Route Planning: The Traveline and Rome2Rio both offer free and detailed online route planning facilities on their websites which may help you find your way to and from your holiday location. Details can be found at: www.traveline.info and www.rome2rio.com


    Rest Days and Extra Nights:

    If you wish to add rest days into your itinerary or add extra nights, please contact us.


    'Accommodation Only' package:

    Some walkers travel very light or want to carry all their belongings with them. We understand that, so why not choose our 'accommodation only' package. We will book your overnight stays in an eclectic mix of accommodations along the route and provide you with location maps for each property, so you won't struggle to find it at the end of a walking day. Please contact us for details.

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