Walking from Robin Hood’s Bay to Whitby lets you explore beautiful traditional seaside towns, a stunning coastline, and architecturally significant monuments.

To get out of town, go down to the seafront and pick up the Cleveland Way. This part of the route is fully paved and snakes up and away from Robin Hood’s Bay onto the moors with the North Sea on the right. 

As you climb, the elevation rises sharply. Eventually you will reach a gate into a field where you have an excellent view of the surrounding scenic countryside and coastline. From the clifftops, you should be able to see a large headland to the south and glimpses of the coastline to the north. 

After some time, the paved path comes to an end, replaced by mown grass. The path is wide but can be quite boggy in places. There are fences protecting the heathland to the left but no barriers preventing you from falling off the cliffside to the right, so be careful. 

As you make your way north along the path, it will frequently turn inland and then back out towards the cliffs again, as the topology changes. In some patches, there are sections of traditional stone walls remaining, though most of them have already collapsed into the sea. 

Eventually, you will come to a series of gently sloping green fields on your left and with some rock formations out to sea where you will get your first glimpse of the white buildings of Whitby. At this point, the footpath becomes a single track hugging the coastline.

If you continue along the Cleveland Way, you will find yourself just outside the ruins of Whitby Abbey. There has been a religious site here since AD 657 when King Oswy of Northumbria founded it. The Gothic structure you see today dates back to the 13th century when the abbey once soared high above the Whitby coast. Unfortunately, centuries of weather, wear and war mean that, today, the building is a shadow of its former self. Even so, the location is still stunning, with exceptional views over the surrounding coastline. 

As you continue towards the heart of Whitby, you will encounter the town’s famous 199 steps. These lead from the abbey at the top of the hill all the way down to the port. 

Interestingly, researchers think that the steps might be even older than the abbey. In the medieval era, they were made of wood. However, in 1774, local builders substituted them for stone, creating something more robust. 

Originally, people believed that climbing the 199 steps was a test of christian faith for those worshiping or praying at the Abbey. However, that story likely developed much later. The steps are necessary because of the shape of the surrounding land.

After a long journey, many walkers are ready for a drink once they get into Whitby. The Whitby Brewery is a popular watering hole, serving a variety of traditional ales and beers. Over the last few years, it has been growing steadily and now it is one of the first most popular places to visit. There are sit-down options and tour tickets are available for those who want to see how ales are made. Popular local beers include Abbey Blonde, Whitby Whaler, Jet Black, Saltwick Nab and more. 

Once you get into the centre of Whitby, you will find several famous fish and chip restaurants, celebrated across the country. Two of the most popular are Quayside which offers sit-down fish and chip dinners and Trenchers which won the UK’s Official Best Fish And Chip Restaurant In 2019. Diners can choose both restaurant and fish and chip takeaway options. 

Those looking for a little action and adventure should check out The Endeavour Experience, open every day from 10.00am to 5:00pm. This attraction offers multiple exhibits, a chance to step aboard the beautiful HM Bark Endeavour commissioned by the Royal Navy in 1768, and a restaurant serving traditional food. There are amenities for young children too, making it suitable for all the family. 

Those staying overnight in Whitby before embarking on the next section of the Cleveland way to Sandsend have a choice of hotels and accommodation. Great options include Bagdale Hall, The Langley Hotel, and the Marine Hotel. Luxury seaside apartments are also available.