The Cleveland Way was the second National Trail in England and was officially opened in 1969. There are many reasons that the Cleveland Way has endured this long… with well-attended paths and signage. It is a quiet, enchanting slice of northern English coastal life. The scenery is stunning with golden beaches stretching between imposing cliffs, where you can drop down into lovely little seaside towns that seem protected from the passage of time. If that isn't reason enough to visit, here are some top sights and experiences along the route!

Helmsley Brewery

This family-run brewery has a mission ‘to make other people as passionate about handcrafted beer from the North Yorkshire Moors’ and offers tours and tastings. All beers contain Yorkshire Malts and at least one English hop, these then get combined with international hops from all around the world to create some flavoursome ales, such as ‘Yorkshire Legend’ or ‘Helmsley Honey’.

Rievaulx Abbey

This impressive site was once one of England’s most powerful monasteries and the first Cistercian abbey in the North of England. The museum tells you about the monks that called this abbey their home, the dramatic fall of the monastery and there are interesting artefacts on display.

Roseberry Topping

Known as Yorkshire’s very own Matterhorn! Although Roseberry Topping is not actually a mountain, it makes for an exciting experience. Once you reach the summit you are rewarded with unique views to the surrounding landscape. You will also find Captain James Cook’s Monument here, one of the world’s most famous explorers who was born in Yorkshire in 1728.

Robin Hood’s Bay

Located on the Heritage Coast of the North York Moors, this charming seaside village makes for a fantastic visit. Hunt for ancient fossils on the sandy beach, wander through its narrow, cobbled streets and visit the friendly cafes, pubs, and restaurants. Relax with a refreshing ice cream and imagine the local history of smugglers, sailors and fishermen that walked the same streets hundreds of years ago.

Whitby Abbey

The remains of Whitby Abbey are perched high on a cliff, offering outstanding views everywhere you look – across the harbour and into the rolling countryside. There are years of history to discover as you wander around the ancient ruins that were the inspiration for Bram Stoker’s gothic tale of ‘Dracula’.

Scarborough Castle

Head towards Scarborough Castle and enjoy panoramic views over the Yorkshire coastline as you step into 3000 years of history. Explore the castle and gain insight into its past, it has seen some of England’s most defining battles! Before continuing along the Way, fuel up with some local treats from the coffee shop at the Master Gunner’s House.

If you would like to ask our team of specialists any questions about this fantastic national trail, please don't hesitate to contact one of our Destination Specialists, who will be more than happy to help and share their walking experiences!