The Cleveland Way

A journey through Yorkshire's pastoral heart, from Irish Sea to North Sea

LengthLength: 109 miles
DurationDuration: 7-10 days
DifficultyDifficulty: Intermediate

From £950 per person

Discover Yorkshire's most breathtaking long-distance trails with Hike Yorkshire's expertly guided multi-day adventures. Our itineraries combine stunning landscapes, fascinating local history, and comfortable accommodation leaving you free to focus on the journey.

check iconQualified mountain leaders and local guides
check iconDaily baggage transfers
check iconCarefully selected accommodation
check iconHistorical and folklore commentary throughout
Jimmy helping hikers on a trail

Do you need a guide?

Hike Yorkshire provides ex-military guides who are highly trained in navigation, first aid, fieldcraft, and fitness. Their local knowledge is invaluable in ensuring your day out is both educational and enjoyable.

Conditions on the hills can change quickly, so taking a well-drilled professional along is the best way to make sure everyone returns safe and happy.

The Cleveland Way is Yorkshire's great circular adventure, blending sweeping moorland ridges with the North Sea's dramatic coastline.

Starting in Helmsley, this route follows Iron Age hill forts, abbey ruins, and purple heather trails before meeting the sea near Saltburn, Whitby, and Scarborough. A journey of big skies, ancient heritage, and seaside charm.

Route Highlights

  • Visit Rievaulx Abbey, one of Yorkshire's most atmospheric ruins.
  • Enjoy panoramic views from Sutton Bank, described by author James Herriot as "the finest view in England."

Sights of Interest

  • Rievaulx Abbey and Mount Grace Priory – echoes of Yorkshire's monastic past
  • Roseberry Topping – Yorkshire's "mini Matterhorn"
  • Staithes & Runswick Bay – colourful fishing villages
  • Whitby Abbey & harbour – gothic grandeur and maritime history
  • Scarborough Castle – Norman fortress with sea views
Cleveland Way scenery

Why Choose the Cleveland Way?

  • IntermediateIdeal for intermediate walkers seeking variety and cultural depth
  • Moors and CoastA rare blend of wild moorland walking and dramatic Yorkshire coastline
  • HistoryAncient paths linking abbey ruins, clifftops, and fishing villages
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