Cleveland Way Trail Holidays
Be inspired with our inspirational short walks and breaks or longer walking itineraries. Use our itinerary planner to create a customised trip, based on your preferences.
Starting in the beautiful market town of Helmsley the Cleveland way takes you across the heather-clad North York Moors to reach the sea. The coastal section offers some of the best coastal walking in the UK. Explore the Cleveland Way for three days, a week or even longer. Find inspiration for your walking adventure using our suggested itineraries, or select one of our bookable itineraries which are highlighted with a star.
Three-to five-day adventures based along sections of the trails that pack in a bit of everything: great hikes plus hands-on experiences, impressive sites, fabulous food and drink and amazing places to stay.
Discover the length and breadth of these impressive trails with walks for all abilities, always accompanied by stunning views and a comfortable place to stay.
Use the map below to help plan your visit. Turn layers of data on and off by ticking or unticking the boxes in the Map Filter. Drag the map and use the Zoom tool to navigate. Select 'Add to Itinerary Planner' to save your chosen points, then scroll down to build your bespoke trip.
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