The cleveland way

Day 1: Helmsley to Osmotherley (Approx. 20 miles)

Start your journey in the picturesque market town of Helmsley. From Helmsley, follow the Cleveland Way trail markers through beautiful moorland, past Rievaulx Abbey, and onto the village of Osmotherley. Osmotherley is a charming village and a great place to spend your first night.

Day 2: Osmotherley to Clay Bank Top (Approx. 10 miles)

From Osmotherley, continue along the Cleveland Way, heading toward the Cleveland Hills. The walk will take you through hilly terrain, and you’ll eventually reach Clay Bank Top. This section offers stunning views of the surrounding landscape

Day 3: Clay Bank Top to Roseberry Topping (Approx. 10 miles)

From Clay Bank Top, continue eastward, following the path through the Cleveland Hills. The highlight of this section is the iconic Roseberry Topping, a distinctive hill that’s worth the climb for its panoramic views. After descending Roseberry Topping, continue on to the village of Great Ayton.

Day 4: Great Ayton to Saltburn-by-the-Sea (Approx. 13 miles)

Leave Great Ayton and head toward the coast. You’ll pass through the Guisborough Forest and walk along the Heritage Coast, offering spectacular views of the North Sea. Your destination for the day is Saltburn-by-the-Sea, a charming seaside town.

Day 5: Saltburn-by-the-Sea to Staithes (Approx. 12 miles)

Continue along the Cleveland Way, walking along the rugged coastline, past cliffs, and through picturesque fishing villages. Staithes is a quaint village with a rich history, and it’s a perfect place to explore and relax.

Day 6: Staithes to Whitby (Approx. 11 miles)

The final leg of your journey takes you to Whitby, a historic coastal town. Follow the Cleveland Way along the coast, passing through Sandsend, and eventually arriving in Whitby. Explore Whitby’s abbey, harbor, and other attractions.

Day 7: Rest day in Whitby

Whitby is a fascinating place with plenty to see and do. Spend a day exploring the town, its historic sites, and perhaps enjoying some seafood by the sea.

Day 8: Whitby to Robin Hood’s Bay (Approx. 7 miles)

On your last day, walk the final stretch from Whitby to Robin Hood’s Bay. The Cleveland Way officially ends at Robin Hood’s Bay, a charming village on the coast.

This is just one example of how you can walk the Cleveland Way. You can adjust the itinerary based on your pace and preferences, and there are also accommodations and facilities along the route to make your journey comfortable. Be sure to check trail conditions and make accommodations in advance to ensure a smooth hiking experience.