The Cleveland Way was established in 1969 and was the second official National Trail of England (the first being Pennine Way). The trail starts in the beautiful market town of Helmsley and follows a well-trodden trail through the heather-clad moorlands of the North York Moors National Park until you reach the coast. From here, the trail runs down the dramatic North Yorkshire Coastline to Filey, taking in iconic villages such as Robin Hood’s Bay and Whitby (famously the home of Whitby Abbey, inspiration for Bram Stoker’s gothic tale ‘Dracula’).
The scenery experienced along the trail is split into two halves. From Helmsley to Saltburn-by-the-Sea, you will explore the inland geography of North Yorkshire, surrounded by the dramatic moorland landscapes and wild vistas, then spending your evenings in quaint villages tucked away in the valleys. From Saltburn-by-the-Sea to Filey, the scenery shifts, and we begin to experience the rugged Jurassic coastline of North Yorkshire. You’ll walk along the cliffs, looking down to the sea and discovering secluded coves and bays. The atmosphere becomes more vibrant, with vivid seaside towns and perhaps an evening drink watching the sunset.
If you love it so much you’re wanting more, you can extend the route and make it a round trip back to Helmsley via the Tabular Hills Walk (please discuss with us when booking). Alternatively, you could embark on the Yorkshire Wolds Way between Hessle and Filey.
We take the stress out of your trip with expert local knowledge, hand-picked accommodation, luggage transfers and detailed support to help you find your way. You will need full walking kit including waterproof jacket and trousers, a small day sack and comfortable walking boots but you will receive a more detailed kit list upon booking. This trip is based on 2 people sharing, so if you are a solo traveller please contact us for further details and we will be happy to help.