02/09/2026
Station Road, Robin Hoods Bay, North Yorkshire, YO22 4RE
Walk the Cleveland Way from Robin Hoods Bay to Whitby â A 109-mile long National Trail in North Yorkshire, England. The trail begins in the historic market town of Helmsley & ends in the coastal town of Filey.
Our journey takes in part of the Cleveland Way, with the starting point at the picturesque old fishing village of Robin Hoods Bay â A maze of narrow, steep, cobbled streets, steeped in smuggling history. A notorious hub where contraband could be moved up the cliff through hidden passages.
Heading in a Northerly direction past the village post office, take a right onto Mount Pleasant South Road. Follow around to the left, then take a right. Youâll pass a sign for both the Cleveland Way and the Cinder Track. The track splits into two â take the upper track to the right side for the Cleveland Way. As you continue along, the track opens up beautifully, where land meets sea. Where the waves of the North Sea continually erode the ever-changing dramatic coastline, that is so fondly known as the East Coast of England.
Along the way youâll pass the Whitby High Lighthouse. A former lighthouse keepers cottage, which has been converted into holiday rentals. A real room with a view!
As you continue to traverse the rugged cliff-top paths, uneven stone steps, grassy tracks & short road sections, youâll soon stumble upon Dracula territory, that is best known as Whitby. As the track nears closer, itâs hard to miss the dramatic remains of the Whitby Abbey â a real eye pleaser. Once you reach Whitby you wonât want to miss a look round the independent book shops, jewellery shops & all else it has to offer.
A moderate grade walk, which is approximately 6.5-7 miles long. It took us around 3.5 hours to complete, which included around a 20 minute break for lunch. I highly recommend having a go. It really is a stunning section of coastline.
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