Cleveland Way National Trail

This is the full 109-mile (175 km) point-to-point Cleveland Way from Helmsley to Filey Brigg, and that distance is one way with no return leg. Guidebooks usually break it into about 9 days. Most walkers go clockwise from Helmsley so the prevailing wind sits behind them along the coast, but either direction works.

• Helmsley to Sutton Bank: past Helmsley Castle and the route start marker, on to Rievaulx Abbey, the wooded Rye Valley and Nettledale, then a climb through Cold Kirby to the Sutton Bank escarpment and the White Horse of Kilburn.
• Hambleton Hills to Clay Bank: the limestone edge and Hambleton Drove Road above Gormire Lake, through Osmotherley, then the Cleveland Hills and five moors, with old mining heritage and a little hands-on scrambling at the Wainstones.
• Urra Moor to Guisborough: the high crossing over Urra Moor at roughly 454 m, the moors' high point, the remote Blowarth Crossing, then down to Kildale and into Captain Cook country past Captain Cook's Monument and Roseberry Topping, on to Guisborough and Saltburn.
• Saltburn to Filey Brigg: clifftop coast by Boulby Cliff, Staithes, Runswick Bay, Sandsend, Whitby and Whitby Abbey, Robin Hood's Bay, Ravenscar, Hayburn Wyke, Scarborough, then Cayton Bay to the finish on Filey Brigg.

Anyone reasonably fit can complete it, but the Cleveland Hills and the coastal cliffs are the hard parts, with repeated steep climbs and descents rather than one long ascent. Surfaces vary a lot: flagged moorland path, stone tracks, grassy field edges, forest road, sand and shingle, plus stretches of lane, village street and town pavement, so this is not a flat or continuously wild route. Moor tops are open and exposed to wind and weather, and the cliff path has unfenced drops in places. The trail is well signed, but carry an up-to-date map or GPS mapping and know how to use it.

You walk from limestone escarpment and heather-covered moor onto Jurassic sea cliffs, and the built history keeps pace: Rievaulx Abbey, the White Horse of Kilburn, Mount Grace Priory near the route, Gisborough Priory, Whitby Abbey and Scarborough Castle, plus alum and ironstone workings along the coast and hills.

Both ends are reachable by public transport, with bus and rail links at Helmsley and rail and bus services at Filey. Intermediate towns and villages give you transport options, food or beds for staged walking. If you are driving, use town parking in Helmsley at the start. Dogs are welcome, but keep them on a lead or under close control throughout for livestock, ground-nesting birds and cliff-edge safety.

A single day section is often the smarter choice. Sutton Bank and the White Horse, the Wainstones ridge, or a coastal stretch such as Whitby to Robin Hood's Bay each deliver the character of the trail in a few hours, and each is easy to reach and to leave.