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great views! Walking Holidays in Northern England on St Cuthbert's Way, St Oswald's Way, Hadrian's Wall Path
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Walking Holidays in the UK Walking Holidays in Cotswolds and Southern England on Cotswold Way, Shakespeare's Way, Thames Path, and more
Walking holidays in Scotland: West Highland Way, Great Glen Way, Arran Coastal Way, and more Walking Holidays in West Country of England: Devon, Cornwall, Somerset and Dorset

Self-Guided Walking Holidays in the UK

Walking holiday on Cleveland Way in Yorkshire Walking holiday on Yorkshire Wolds Way in UK
Walking holidays on Dales Way in England Walking Holidays on Hadrian's Wall Path Walking Holidays on the Herriot Way in Yorkshire Walking holiday on Leeds and Liverpool Canal in UK Walking Holidays on Northumberland Coast Path Walking Holidays on the Richmond Way
Walking holidays on Cumbria Way in Lake District Walking holidays on St Cuthbert's Way Walking holidays on St Oswald's Way

Walking Holiday in Northern England on
Cleveland Way
from Helmsley to Filey
via Rievaulx Abbey, Sutton Bank, Whitby, Robin Hoods Bay
108 miles

Walking holiday on Cleveland Way with Lets Go Walking
Walking Holidays on Cleveland Way with Lets Go Walking Online Booking Available
Whitby on Cleveland Way walking holiday  with Let's Go Walking
Staithes on Cleveland Way walking holiday  with Let's Go Walking
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 walking trail is clearly way-marked
to provide reassurance on your hiking vacation in Northern England.
Cleveland Way
Helmsley to Filey
12 day itinerary
Suggested Tour Duration:
10 days walking
11 nights
Total Distance:
108 miles / 175 kms
Min/max daily distance:
9/13 miles
Average Daily distance:
11 miles
easy to moderate

North York Moors,Rievaulx Abbey
White Horse at Kilburn, Mount Grace Priory
This route connects with:
Yorkshire Wolds Way
  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

What's included
in your UK walking holiday
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
  • transfers as specified
  • support should there be any problems on route
  • OS maps and detailed itineraries
  • Guide book to Cleveland Way
You can walk this hiking tour over 10 days at about 11 miles per day.

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

The above 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 England or the UK. 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 Extras
for your UK Walking Holiday
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

Cleveland Way 12 day itinerary:
10 days walking and 11 nights accommodation
single occ
solo traveller
Book Cleveland Way walking holiday online now
All prices subject to change
Extra nights from £48 per person per night
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
Contact us about your walking holiday now
How to get there
By Plane to Humberside International Airport, Leeds-Bradford International Airport or Manchester International Airport, where we can arrange transfer to Hull/Hessle
By Car to Helmsley where parking is available
By Train / Bus to Helmsley
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