Quick Link for Cleveland Way, part of the England Coast Path

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The Cleveland Way
Walking Holiday in
Yorkshire Northern England

Nt Cleveland Way Guide Letsgowalking

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The Cleveland Way
Walking Holiday in The North Yorkshire Moors and along the Yorkshire Coast in Northern England
from Helmsley to Filey
via Rievaulx Abbey, Whitby, Staithes, Robin Hood’s Bay and Scarborough

The Cleveland Way is a 108 mile National Trail
through the unspoilt countryside of the North York Moors in Northern England.
This walking trail is a great introduction to long-distance walking holidays and is suitable for every level of walking ability.
The Cleveland Way forms part of the England Coast Path and connects with the Yorkshire Wolds Way at Filey.

We offer 1 suggested itinerary for the Cleveland Way:

  • 12 day holiday, 108 miles

Please see details below

Our self-guided walking holidays are designed with your comfort and enjoyment in mind and can be tailor-made to your own personal requirements.

The routes are clearly way-marked to provide reassurance on your hiking vacation.

We use high quality guest houses, inns or small hotels with en-suite or private bathroom to ensure you are well rested each night after a busy day hiking and sightseeing. Rest assured that all our accommodation walking holiday providers are hand-picked and offer you that famous British hospitality.

Special diets can be catered for, including vegetarian, vegan, and gluten free.

We organize the luggage transfer so your bags are at your next accommodation when you arrive.

Let’s Go Walking has developed one of the largest selection of walking holidays and our offices are staffed 9am to 9pm to ensure your walking holiday runs without a hitch.

This walking holiday in the UK operates March to October and in either direction.

The daily distances are only a suggestion. If you would like to walk longer or shorter distances, we can arrange that too.
Our stated distances include mileage to the accommodation or pickup point and so may not agree with the guide book mileages.
Rest days can be taken in any location.

Why not combine this walk with a hiking tour in another part of the UK or Ireland. Our staff will be happy to advise on necessary transfers.

Online booking available.
A deposit of £85 per person is required to secure the booking, with the balance due 6 weeks before departure.
Optional extra days and accommodation upgrades can be added during the booking process online.

The Cleveland Way 12 day itinerary
 from Helmsley to Filey
10 days walking and 11 nights

Suggested Itinerary:
Day 1: arrive Helmsley
Day 2: Helmsley to Sutton Bank            10 miles
Day 3: Sutton Bank to Osmotherley      12 miles
Day 4: Osmotherley to Clay Bank           11 miles
Day 5: Clay Bank to Kildale                      9 miles
Day 6: Kildale to Skelton                          13 miles
Day 7: Skelton to Staithes                         11 miles
Day 8: Staithes to Whitby                        12 miles
Day 9: Whitby to Ravenscar                    10 miles
Day 10: Ravenscar to Scarborough         10 miles
Day 11: Scarborough to Filey                    10 miles
Day 12: depart Filey


single occ

solo traveller

All prices subject to change

Extra nights from £48 per person depending on location

Suggested Tour Duration:
11 nights, 10 days walking
Total Distance:
108 miles/175 kms
Min/max daily distance:
9/13 miles
Average Daily distance:
11 miles
Easy to Moderate
North Yorkshire Moors, Rievaulx Abbey
North Yorkshire Moors Steam Railway
White Horse at Kilburn
Mount Grace Priory
This path connects with:
Yorkshire Wolds Way

What’s included
in your UK walking holiday
in The Yorkshire Dales and The Yorkshire Coast Northern England on The Cleveland Way

  • accommodation at high quality guest houses, inns or small hotels on a bed and breakfast basis
  • room with en-suite or private bathroom, tea and coffee making facilities
  • daily luggage transfer
  • support should there be any problems on route
  • detailed itineraries
  • OS 1:25,000 map
  • guide book to The Cleveland Way

Optional Extras
for your UK Walking Holiday
in The Yorkshire Dales and The Yorkshire Coast Northern England on The Cleveland Way

  • upgrade to the region’s most elegant, prestigious and famous hotels, where available
  • transfers back to car or station
  • parking facilities
  • rest days
  • inn to inn walks

What’s not included
in your UK walking holiday
in The Yorkshire Dales and The Yorkshire Coast Northern England on The Cleveland Way

  • lunches and dinners
  • travel insurance

Lunches and Dinners
These are not included.
Evening meals
These are available at overnight locations, either at your accommodation or in the town/village.
Packed lunches
These can be provided by your accommodation or can be obtained from a local store, or cafe or inn along the route.

Holiday Travel Insurance
We require that you take out holiday insurance as Let’s Go Biking Ltd accepts no liability for the following:
cancellation, personal accident, illness, loss/theft of personal possessions and/or money, and any unforeseen circumstances, especially travel delays.

This is in addition to our existing
booking conditions.

Telephone Lines are open 7 days a week.

UK +44 (0)1837 880075
or +44 (0)207 193 1252

9am to 9pm
US +1 (646) 233-1541
New York 5 hours behind UK time: 4am to 4pm EST
AUS +61 (02) 8006 0182
Sydney 10 hours ahead of UK time: 7pm to 7am EADT
CAN +1 (647) 4786251
Toronto 5 hours behind UK time: 4am to 4pm EST

How to get there:

  • By Plane to Humberside International Airport, Leeds Bradford or Manchester where we can arrange transfer to Helmsley
  • By Car  to Helmsley where parking is available
  • By Train / Bus to Helmsley

We offer National Trail walking holidays in England and Wales in the UK.  This is one of our categories of walking holidays.

We have moorland walking holidays in the UK in England, Scotland, Wales, Northern Ireland,  and Ireland.  This is one of our categories of walking holidays.