Contours Walking Holidays ... a step ahead!

Share |
Contact Us

Contours Walking Holidays

Cleveland Way

A self-guided walking holiday around the North York Moors National Park and the Cleveland Heritage Coast.
Cleveland Way Map

click on the map to enlarge

The Cleveland Way is a horseshoe-shaped route around the edge of the North York Moors National Park. Beginning in the old market town of Helmsley, the trail follows the western escarpment of the North York Moors to meet the coast at Saltburn-by-the-Sea, and then takes in the whole of the North Yorkshire and Cleveland Heritage Coast to finish at the Victorian seaside town of Filey.

The first half of the Cleveland Way through the North York Moors from Helmsley to Saltburn-by-the-Sea passes through woodland, lush green dales and spectacular heather moorland. Around every corner lies something of interest; a ruined castle, an ancient abbey, the White Horse of Kilburn, an old drove ‘road', a priory, ancient stone markers and crosses, rocky escarpments with far-reaching views, traces of alum, jet and ironstone mining, prehistoric burial mounds, or a grouse flying across the path.

The second half of the Cleveland Way from Saltburn-by-the-Sea to Filey, follows a rugged coast of high cliffs, wide sandy bays and wooded ‘wykes'. Picturesque fishing villages with steep, winding streets and tightly packed cottages; the old whaling port of Whitby, with its imposing abbey, Captain Cook Museum and St Mary's Church whose interior was altered in 1612 to resemble the lower deck of a wooden sailing ship, add to the charm of this delightful walk.

Holiday Options
  • Cleveland Way
    Helmsley to Filey
    110.5 miles (176 km)
    7 to 10 walking days
    from £500 per person
    View tour details
  • North York Moors Section
    Helmsley to Saltburn-by-the-Sea
    57 miles (91 km)
    5 walking days
    £370 per person
    View tour details
  • Heritage Coast Section
    Saltburn-by-the-Sea to Filey
    53.5 miles (85.5 km)
    5 walking days
    £375 per person
    View tour details
Customers Photo Gallery

Click here for more images of this holiday

Holiday Highlights

  • Visiting locations rich in history and heritage, from Rievaulx Abbey, Scarborough Castle and Mount Grace Priory to the inspiration for Dracula in Whitby.
  • Spotting the variety of wildlife, from grouse in the heather moors to the sea birds along the coastline.
  • Being rewarded by dramatic coastal views as you reach the North Yorkshire coastline on the approach to Filey.

Cleveland Way

A walk from Helmsley to Filey around the North York Moors and the Heritage Coast.
Total Distance 110.5 miles (176 km)
Start and Finish Helmsley to Filey
Availability 27th March to 11th October
click on a photo to enlarge
Staithes © BOV
The Cleveland Way © Countryside Agency/Mike Kipling
Tour Code Itinerary Tour Price    
CLEVW1 8 nights, 7 days walking £500 per person More Information Book Online
CLEVW2 10 nights, 9 days walking £615 per person More Information Book Online
CLEVW3 11 nights, 10 days walking £670 per person More Information Book Online
Our prices are based upon two people sharing a room. If you are walking on your own, or are part of a group, but require a room of your own, the following charges apply:
Solo Walker Supplement: £25 per person / per night
Single Supplement: £12 per person / per night
You can add rest days at any of the overnight stops. For each extra night add £48 per person. All of our prices are in British pounds (£). Use our currency converter to convert British pounds (£) to your country’s currency.
The price that you pay includes accommodation on a bed and breakfast basis, door to door luggage transfers for every day of your tour, maps, guidebooks and a tour pack detailing specific information about your holiday.

Don’t have the time for the complete walk?

We also offer The Cleveland Way in two sections, each of which is an excellent walk in its own right, giving those with less time the opportunity to complete the trail in stages.

  • North York Moors Section, from Helmsley to Saltburn-by-the-Sea

  • Heritage Coast Section, from Saltburn-by-the-Sea to Filey

Cleveland Way - North York Moors Section

Helmsley to Saltburn-by-the-Sea along the western escarpment of the North York Moors.
Cleveland Way - North York Moors Map

click on the map to enlarge

Total Distance 57 miles (91 km)
Start and Finish Helmsley to Saltburn-by-the-Sea
Availability 27th March to 11th October

The North York Moors Section of the Cleveland Way begins in Helmsley and takes in the largest expanse of heather moorland in the United Kingdom on its route to Saltburn-by-the-Sea. From the medieval castle of Helmsley, the trail visits a series of interesting locations, including the ruins of Rievaulx Abbey and the White Horse of Kilburn. The trail then passes high through Sutton Bank on the edge of the Hambleton Hills, where there are spectacular views of the surrounding countryside.

From Sutton Bank, the trail passes to Osmotherley, high above Gormire Lake, on its route to Claybank Top, Ingleby Cross and Kildale, typical northern towns and villages set in stunning surroundings. The distinctive landmark of Roseberry Topping comes into view on the final stretch to Saltburn-by-the-Sea where, after a short descent, the North Sea offers its greeting as you complete your walk.

Holiday Highlights

  • Spotting gliders from Sutton Bank, with outstanding views over the Vale of York.
  • Reaching the North York Moors’ highest point on Urra Moor with far reaching views across the Cleveland Way.
  • Arriving in the Victorian seaside resort of Saltburn-by-the-Sea and strolling along its pier, the most northerly surviving British pier.
Tour Code Itinerary Tour Price    
CLEVWM 6 nights, 5 days walking £370 per person More Information Book Online
Our prices are based upon two people sharing a room. If you are walking on your own, or are part of a group, but require a room of your own, the following charges apply:
Solo Walker Supplement: £25 per person / per night
Single Supplement: £12 per person / per night
You can add rest days at any of the overnight stops. For each extra night add £48 per person. All of our prices are in British pounds (£). Use our currency converter to convert British pounds (£) to your country’s currency.
The price that you pay includes accommodation on a bed and breakfast basis, door to door luggage transfers for every day of your tour, maps, guidebooks and a tour pack detailing specific information about your holiday.

Cleveland Way - Heritage Coast Section

Saltburn-by-the-Sea to Filey along the Heritage Coast of North Yorkshire and Cleveland.
Cleveland Way - Heritage Coast Map

click on the map to enlarge

Total Distance 53.5 miles (85.5 km)
Start and Finish Saltburn-by-the-Sea to Filey
Availability 27th March to 11th October

The Heritage Coast Section of the Cleveland Way begins in the Victorian seaside town of Saltburn-by-the-Sea and follows the rugged cliffs to Filey.

From Saltburn, the trail visits Boulby where a backdrop of wildflowers opens out to far reaching views from the highest cliffs in England.

Soon, the trail enters Whitby along a sandy beach and with Whitby Abbey and St Mary's Church dominating the view, the old whaling port offers a fascinating cultural heritage to explore.

From here, the trail joins the route of the Coast to Coast in Robin Hood's Bay, before continuing on to the bustling seaside town of Scarborough, where its ancient castle provides wonderful panoramic views over the Yorkshire coastline. From here, a day of wonderful coastal walking leads to Filey, where the rocky peninsular of Filey Brigg marks the end of the Cleveland Way.

This section, marked by picturesque fishing villages and with a wealth of maritime and literary history, is a fantastic way to experience the Cleveland Way.

Holiday Highlights

  • Admiring the extensive views from Boulby, the highest cliffs in England.
  • Wandering through the fascinating features of Whitby, including the whalebone arch, 199 steps, Whitby Abbey and St Mary’s Church.
  • Experiencing the many quaint fishing villages and lively coastal towns along this spectacular piece of Yorkshire coastline.
Tour Code Itinerary Tour Price    
CLEVWC 6 nights, 5 days walking £375 per person More Information Book Online
Our prices are based upon two people sharing a room. If you are walking on your own, or are part of a group, but require a room of your own, the following charges apply:
Solo Walker Supplement: £25 per person / per night
Single Supplement: £12 per person / per night
You can add rest days at any of the overnight stops. For each extra night add £48 per person. All of our prices are in British pounds (£). Use our currency converter to convert British pounds (£) to your country’s currency.
The price that you pay includes accommodation on a bed and breakfast basis, door to door luggage transfers for every day of your tour, maps, guidebooks and a tour pack detailing specific information about your holiday.
Contact Us ... click here
  • Home
  • Holiday Location Map
  • Holidays in South of England
  • Holidays in the North of England
    • Alternative Coast to Coast Walk
    • Bob Graham Round (NEW for 2013)
    • Cleveland Way
    • Coast to Coast Walk
    • Cumberland Way
    • Cumbria Way
    • Dales Way
    • Dales High Way (NEW for 2013)
    • Furness Way
      • Hadrian's Wall Path
        • Walking from East to West
        • Walking from West to East
    • Herriot Way
    • Lady Anne's Way
      • Lake District Short Breaks
        • Coniston Water Round
        • Cumbria Way Highlights
        • North Lakes Short Breaks
        • South Lakes Short Breaks
        • West Lakes Short Breaks
        • East Lakes Short Breaks
        • Lakeland's Three Passes Walk
        • St Bega's Way
        • Ullswater Round
        • Westmorland Way
        • Windermere Way
    • Lakeland Round
    • Nidderdale Way
    • Northumberland Coastal Path
    • Pennine Way
    • Pride of the Peak Walk
    • Six Dales Trail
    • St Oswald's Way
    • Swale Way
    • Teesdale Way
    • Westmorland Way
    • White Peak Way
    • Windermere Way
      • Yorkshire Dales Short Breaks
        • Three Dales Way
        • Dales Way Highlights
        • Six Dales Trail
    • Yorkshire Wolds Way
  • Holidays in Wales
  • Holidays in Scotland
  • Holidays in Ireland
  • Short Breaks and Weekends

Find a Holiday

Destination

Holiday Length

Our Blog Feed

Facebook   Google+   Email   RSS

Our Blog Feed

Members Area ... click here
  • About Our Holidays
  • Frequently Asked Questions
  • Weather Information
  • Group Discounts & Bespoke Tours
  • Useful Links
  • Testimonials
  • Privacy Policy
  • Booking Conditions
How to Book... click here
  • A Guide to Our Holidays
  • Competitions
  • Photo Galleries
  • Writing Collection
  • Challenge for Charity
  • Dog Friendly Walking Holidays
Gift Vouchers ... click here
Why book with Contours Walking Holidays?
  • Outstanding reputation.
  • Choice.
  • Flexibility.
  • Walking holidays to suit everyone.
  • Local experts.
  • Quality accommodation.
  • Holiday documents.
  • Reliable luggage transfer.
  • Unbeatable value for money.
  • Financial security.
  • Group discounts.
  • No hidden charges.
  • Outstanding customer service.
  • Emergency support.
  • Loyalty scheme.

Find out more...

Download our Brochure

Mr Mountford. Isle of Wight.

A really interesting, varied, scenic route. High quality accommodations, some of which were outstanding. All wonderful but I particularly enjoyed the Coastal section. A thoroughly enjoyable and well organised holiday. Thank you.

© Contours Walking Holidays    Tel: +44 (0) 1629 821900    Email

Home    Holiday Location Map    Site map    Contact us