Landmark Locations on the Cleveland Way

By Mark Wright

The Cleveland Way National Trail is an enthralling long-distance walk that travels through the breathtaking landscapes of the North York Moors and along the rugged Yorkshire coastline. The 109 mile route offers an enchanting blend of natural wonders, historical landmarks, and coastal charm.

Walkers on the Cleveland Way can explore medieval castles, magnificent abbeys, dramatic cliffs, and picturesque fishing villages. The trail’s diversity, including serene moorland expanses and dramatic coastal panoramas, offers an outstanding adventure for those seeking a connection to both nature and history. Let’s take a look at some of the landmark locations you’ll experience on your journey.

Helmsley Castle

The Cleveland Way begins in the charming market town of Helmsley. Here, you can explore the historic Helmsley Castle. This 12th-century fortress boasts a rich history, playing a role in the English Civil War. Its impressive walls and towers provide visitors with a fascinating insight to medieval life and architecture. The site also features a beautiful walled garden filled with a fabulous variety of plants and flowers. Helmsley Castle is a fantastic starting point for your journey along the Cleveland Way, allowing you to step back in time and appreciate the architectural and historical heritage of this magnificent region.

Rievaulx Abbey

Just a few miles into the trail, nestled in the tranquil Rye valley, sits Rievaulx Abbey. This hauntingly beautiful Cistercian monastery was founded in the 12th century. The extensive ruins of the abbey are remarkably well-preserved and provide a glimpse into the life of the monks who once inhabited it. Known for its tranquil setting and architectural grandeur, the abbey was once one of the most powerful and influential in England. Visitors can explore the towering arches, intricate stonework, and the remains of the church, chapter house, and cloister. The tranquil atmosphere and picturesque setting makes Rievaulx Abbey a place of historical and spiritual significance.

Sutton Bank

Offering breathtaking views over the Vale of York, this high escarpment, proclaimed by the celebrated author and veterinarian James Herriot as “England’s finest view”, is a highlight of the Cleveland Way. From this iconic vantage point the sweeping views stretch far and wide, showcasing the natural beauty of the North York Moors National Park. Sutton Bank is a perfect place to sit and appreciate the splendour of nature and the vast expanse of the English countryside. Walkers will record Sutton Bank as an incredibly memorable and inspirational stop along the trail.

Captain Cook Monument

This wonderful monument commemorates the renowned British explorer, Captain James Cook, who is celebrated for his significant contributions to the field of navigation and exploration during the 18th century. Erected in 1827, on the 100th anniversary of Captain Cook’s first voyage to the South Seas, the monument consists of an elegant obelisk made of sandstone and stands at a height of approximately 60 feet. Its location, on Easby Moor, provides spectacular panoramic views of the Yorkshire coastline, the North Sea, and the surrounding countryside.

Roseberry Topping

Although not directly on the trail, Roseberry Topping is a distinctive local landmark worthy of exploration. It’s an intriguing geological formation, characterised by its half-cone shape summit and jagged cliff. Those who wish to add an additional adventure to their Cleveland Way journey should make time for this excellent little detour. Reaching the summit of this miniature mountain is a hugely rewarding experience, with stunning panoramic views of the surrounding landscape. From Roseberry Topping, you can admire the beauty of the Cleveland Plain and the North York Moors.


The picturesque coastal town of Whitby has a rich history and an abundance of attractions. The town is famous for its stunning gothic abbey, which served as inspiration for Bram Stoker’s Dracula. Visitors can climb the 199 steps to the abbey for captivating views of the town and out over the North Sea. Whitby’s charm extends to its lively harbour, where you can watch fishing boats come and go, sample fresh seafood at local restaurants, and explore the maritime heritage at the Captain Cook Memorial Museum. The town also boasts cobbled streets lined with quaint shops, boutiques, and tearooms. The beach is perfect for a leisurely evening stroll if you still have a few more miles in you.

Robin Hood’s Bay

This charming fishing village is a quintessential coastal gem. Soaked in history and full of character, its steep, narrow streets wind their way down to a picturesque harbour. The area is renowned for its smuggler heritage, and you can learn about this history at the Robin Hood’s Bay Museum. The bay’s rugged shoreline also provides opportunities for fossil hunting. Its historic buildings, welcoming pubs, and coastal setting make it an enchanting stop on your Cleveland Way journey, offering a taste of traditional English coastal life. Make sure you sample some of the delicious seafood available to you.

Scarborough Castle

Perched on the headland with a commanding view overlooking the town of Scarborough and the North Sea is the former medieval royal fortress, Scarborough Castle. This historic site has hosted an Iron Age settlement, Roman signal station and an Anglo-Scandinavian settlement. The castle itself has a fascinating history dating back to the 12th century and was strategically significant during many conflicts, including the English Civil War. Visitors to Scarborough Castle can explore the well-preserved ruins, including the keep, the Roman signal station, and the curtain walls. The site offers an immersive journey through time, allowing you to imagine the lives of those who once inhabited and defended the castle.

Filey Brigg

This natural rock formation extending into the North Sea is a place of immense natural beauty and intrigue, providing a natural contrast to the many historic and architectural landmarks along the trail. The rocky outcrops are home to various marine life, with the tidal pools and rock formations providing great opportunities for exploration and discovery. Filey Brigg is also a popular destination for birdwatchers, as it serves as a haven for a variety of seabirds and shorebirds. During migratory seasons, it’s a fantastic location for observing these fascinating birds in flight. Filey Brigg’s rugged coastal beauty, coupled with its diverse ecosystem, makes it a must-visit location on the Cleveland coast.


The Cleveland Way ends in the charming seaside town of Filey. Renowned for its sandy beaches and Edwardian architecture, it’s a lovely place to relax after completing the trail. Hopefully you’ll have a few miles left in your legs to enjoy a stroll along the delightful promenade. The town retains a pleasant, bygone feel. Quaint shops, tearooms, and seafood restaurants line the streets, providing a taste of traditional seaside life.

These landmarks represent just a fraction of the magnificence you’ll encounter on the Cleveland Way. The trail encompasses a diverse range of landscapes and historical sites, making it an outstanding long-distance trail for those who appreciate natural beauty and heritage. For further information on the Cleveland Way and to book your 2024 adventure email u[email protected] or call us on 017687 72335 to speak with one of our walking holiday experts.