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01707 817260
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Call us on 01707 817260

  • Monday - Friday9am - 5pm
  • Saturday9am - 1pm
  • SundayClosed
  • Bank HolidaysClosed

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The Cleveland Way National Trail

Some of the most varied and impressive scenery on a long-distance path in England, walking from Helmsley to Filey in North Yorkshire.

  • Half Board

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What does this mean?

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Overview

Holiday Highlights

  • Dramatic clifftop walking with views over the North Sea.
  • Robin Hood's Bay with its cliff-hanging cottages.
  • A walk of contrasts through glorious North Yorkshire - wild moorlands, superb coastal views & dramatic cliff tops.
  • The remains of the Rievaulx Abbey and the gothic 13th century Whitby Abbey.

Commencing in the delightful market town of Helmsley, nestled on the southern edge of the North York Moors, our clockwise route unravels a tapestry of England's most captivating and varied scenery. En route, you'll encounter several iconic highlights, including the renowned Sutton Bank with its striking White Horse etched into the hillside, the distinctive silhouette of Roseberry Topping, the haunting ruins of Whitby Abbey atop a windswept hill, the postcard-perfect harbor village of Staithes, the vibrant seaside hub of Scarborough, and the well-loved coastal town of Filey.

This 109-mile path is conveniently divided into nine manageable day walks. The journey is a harmonious blend of inland exploration, venturing northward through the scenic Cleveland Hills to meet the coast at Saltburn. From there, the path traces a southerly route, unveiling the picturesque charm of Staithes, leading to the historic gems of Whitby, Scarborough, and culminating in the vibrant allure of Filey.

Each leg of the journey offers a unique blend of terrain and vistas, ensuring that every step is a revelation. We've thoughtfully selected two hotels in close proximity to the path, providing seamless transportation to and from the trailheads as needed. This means you can enjoy the convenience of unpacking just once and carrying no more than a day sack. Our chosen accommodations prioritise comfort and minimise travel time, allowing you to focus on the breath-taking journey ahead.

  • Half board en suite accommodation in two centres
  • All local transport required for the itinerary by private coach
  • Private bus transfer to pick up your car at the end of the holiday, if required
  • Services of a Classic Tour Leader
  • Entrance fees (unless otherwise specified)
  • Personal expenses (such as your bar bill)
  • Lunches
  • Discretionary tips
  • Optional excursions
  • Travel insurance

Holiday Information

Click the button below for a detailed Holiday Information Sheet containing all the particulars about this trip.

NOTE: Itineraries and Holiday Information Sheets can vary by a specific date chosen

View Holiday Information Sheet
Field of heather blooming during sunset, Ravenscar, North York Moors national park, Robin Hoods Bay
Cleveland Way path running along the edge near Clay Bank revealing Yorkshire countryside, United Kingdom
Coastal view of the Cleveland Way path in North Yorkshire
The Cleveland Way walking trail at Sutton Bank in the North York Moors with wooden signpost and background of expansive green countryside landscape
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Itinerary & Travel

Itinerary Details

Whilst every effort will be made to adhere to the outlined itinerary and advertised programme, local conditions can change due to weather or other unforeseen circumstances. This may mean that routes and timings need to be amended or the order of days may change, sometimes at short notice.

Accommodation

Accommodation information

Below is the accommodation featured on this holiday across all departure dates. Please refer to the Itinerary for more detail about each night's accommodation for each departure date.

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