Cleveland Way Guided Walking Holiday

Moorland ridges and North Sea clifftops, from Helmsley to Filey.

Length: 109 miles

Duration: 7 to 10 days

Difficulty: Intermediate

From £950 per person

Experienced guides, including qualified Mountain Leaders

Local B&Bs and inns booked for you

Daily luggage transfers

Guided every day, or self-guided with support

The walk

The Cleveland Way is one of England's original National Trails, opened in 1969, and one of the most varied long-distance walks in the country. For the first half it follows the western and northern edges of the North York Moors, high open heather moorland with views for miles. Then it reaches the sea at Saltburn and turns south along the clifftops, through fishing villages and past Whitby Abbey, to finish at Filey Brigg.

Abbeys and priories, Iron Age forts, Captain Cook country, smugglers' coves and some of the highest sea cliffs on England's east coast. Two very different walks joined into one.

How it works

Tell us when you would like to walk, how many of you there are and how many days you would like to take, and we build the trip around you.

We book your accommodation in comfortable local B&Bs and inns along the route, supporting the small businesses that keep the moors and the coast alive. Your luggage is moved between each night's stop, so you only carry what you need for the day. Breakfast is included at most places, and packed lunches can be arranged.

A Hike Yorkshire guide walks with you every day, handling the navigation and sharing the history, folklore and wildlife of the route. If you would rather walk on your own, we can set you up self-guided, with our team meeting you at checkpoints along the way to resupply.

We can also arrange transfers to the start in Helmsley and from the finish at Filey.

The route

Daily stages are typically between 9 and 15 miles, depending on how many days you take. These are the main stops along the way.

Helmsley to Sutton Bank: From the market town of Helmsley and its ruined castle, the route passes the great Cistercian ruins of Rievaulx Abbey before climbing to Sutton Bank, often called the finest view in England, and the Kilburn White Horse cut into the hillside.

Sutton Bank to Osmotherley: North along the Hambleton Hills on an old drovers' road, with the Vale of York spread out below, to the village of Osmotherley and nearby Mount Grace Priory.

Osmotherley to Kildale: The most dramatic moorland section, a roller coaster along the northern escarpment over Carlton Bank, Cringle Moor and the Wainstones, with views across Teesside to the sea.

Kildale to Saltburn: Past Captain Cook's Monument on Easby Moor and the distinctive summit of Roseberry Topping, then down through Guisborough Woods to the Victorian seaside town of Saltburn.

Saltburn to Whitby: Onto the coast, over the high cliffs at Boulby to Staithes, where a young James Cook first worked by the sea, then Runswick Bay and Sandsend into Whitby, with its abbey ruins and 199 steps.

Whitby to Filey: South past Robin Hood's Bay, once a smugglers' haven, over Ravenscar and into Scarborough beneath its castle, then finally along the cliffs to the long rocky finger of Filey Brigg.

Fitness and terrain

The Cleveland Way suits regular walkers who are comfortable with several consecutive days of walking. The moorland section has some steep climbs and descents along the escarpment and is exposed to the weather. The coastal half follows clifftop paths with frequent short climbs in and out of valleys and villages.

Getting there and home

Helmsley has no railway station; the nearest stations are Thirsk and Malton, both connected by bus. Filey has a station on the Yorkshire Coast line to Scarborough and Hull. We are happy to arrange transfers at either end.

Pricing

Prices start from £950 per person. Every trip is tailored, so the final price depends on your group size, how many days you take, whether you walk guided or self-guided, your food requirements and any transfers you need. Tell us what you have in mind and we will come back with a quote.