The Cleveland Way: 9 days

  • Duration 9 Days / 8 Nights
  • Grade
  • Start / Finish Helmsley / Filey
  • Distance 177 km / 110 miles
  • Trip Style Self Guided
  • Availability
  • Availability
    April - September
  • Price From $996


The Cleveland Way will take you through varied and beautiful landscapes. Explore stunning moors, long coastlines, ancient castles and charming fishing villages.

This walking holiday will take you through the North York Moors National Park, where wildlife and cultural heritage blend in to give you a unique experience from Helmsley, where you can visit the National bird of Prey Centre and Helmsley Castle, to Filey.

Finish your tour on the Cleveland Way in Filey, a town with a long golden beach where you can spend the day in the sun.  

  • Walk the Black Hambelton Plateau, which rises up to 399 metres high.
  • Roseberry Topping will be part of this route, a hill known as the Yorkshire Matterhorn.
  • Enjoy Whitby's blue flag-winning beaches, representative of sustainable tourism.
  • Visit the ruins of Rievaulx Abbey.

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    • Accommodation
    • Breakfasts
    • Baggage transfer service
    • Information dossier with maps and route details
    • 24-hour telephone support
    • Taxes included


    • Travel to the beginning and end of your walk
    • Personal equipment
    • Unspecified meals
    • Tourist taxes


    • Travel insurance
    • Cancellation insurance
    • Additional nights before, during or after the tour
    • Improved hotel room upgrades (if available)


    General information

    The accommodations with which we collaborate have a private bathroom and all the necessary services to ensure the best comfort available.

    Our team checks in situ the quality of all the accommodations offered, so that you have an unforgettable experience during your trip.

    The accommodation that we will book for your trip will be selected taking into account our commitment to you: guaranteeing comfort, calm and enjoyment throughout your trip.

    We work with quality hotels and country cottages with limited capacity, so we invite you to confirm your reservation as soon as possible.

    The name of each accommodation will be provided to you a few weeks before your trip begins.

    Room types

    It is possible to book this journey in single, double or triple rooms.

    All rooms have private bathrooms.


    Travel & Transfers

    We recommend starting your trip at Leeds Bradford International Airport, where you can take a train to Malton, then you can head to Helmsley by bus or taxi.

    If you're travelling by train, head to Malton station and take a taxi or bus to get to your destination.

    At the end of your route, you will be able to head to Filey train station, where there are several routes to all parts of the UK.

    To return to Hemsley, first take the train to Malton and then a bus or taxi.


    We recommend that you book as soon as you are sure about your dates, as accommodation can fill up very quickly in this area.

    This walking holiday is available between spring and autumn, from April to October.

    Traditionally, the busiest months for tourists are April and May when considering the weather to be more favourable.

    This route has a low to average level of difficulty, with quiet journeys and some stretches of walking through steep sections, steep roads and heights reaching 1,490 feet above sea level.

    To make the most of this route we recommend you exercise regularly for a couple of months before starting it.

    Yes, it's included. We will transfer the luggage between each accommodation according to your itinerary. Each person can take a suitcase up to 20 kg (45 lbs).

    Once you make your reservation we will send you all the detailed information about the specific equipment you need for this route, considering recommendations for shoes, boots, clothes and a day-to day backpack.

    You can call us to arrange a private transfer for you.

    If you prefer, you can also use public transport or local taxis to get to your next accommodation.