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Hike empty hills, majestic moors and golden coast — Cleveland Way

Stephen Tierney. (CC BY-NC-SA 2.0)

Hike empty hills, majestic moors and golden coast — Cleveland Way

Hiking Collection by Kit P

7

Tours

48:56 h

108 mi

11,300 ft

From wild heather moorland to golden coastline, the ever-contrasting Cleveland Way is a heart-stealing hike of two halves.

The 109-mile (175 km) route, which starts in Helmsley and ends in Filey, explores two very different sides of the North York Moors National Park. The inland section takes you through the wild landscape of the Cleveland Hills and onto the remote North York Moors. This section provides spectacular views and a real sense of tranquility and isolation.

The coastal section follows the shoreline from Saltburn to Staithes, Whitby to Scarborough, and onto Filey. The landscape along this section is one of hidden coves, sleepy fishing villages, golden beaches and Victorian seaside resorts. Often, it feels like time has been standing still for hundreds of years.

On the moorland section, keep a look-out for red grouse, curlews, emperor moth caterpillars and butterflies. Mice, voles, lizards, and other small mammals that live here are prey for the adder, Britain's only poisonous snake. If you walk quietly on a sunny day, you might spot one snoozing on a rock in the sunshine.

As you hike along the coast, watch out for seabirds such as great cormorants, shags, puffins, guillemots and gulls. From June until November, you can observe white-beaked dolphins and minke whales as they follow the shoals of North Sea mackerel and herring swimming south from the Arctic.

In this Collection, I've broken the Cleveland Way into seven stages. This is ambitious, but possible if you are an experienced hiker with a good level of fitness. As three of the stages are very challenging—20 miles (32 km)—I've listed suggestions on how to split them, which makes for a leisurely 10 day itinerary. Of course, you can split up each stage into as many days as you're comfortable with. You can also walk any single stage, or a couple of stages, in isolation.

Every stage finishes close to accommodation, even if there are only a few options. However, places to stay are not abundant so it's worth planning in advance and scheduling any rest days accordingly. There are quite a few campsites near the route too, should you want to bring your tent.

If you're planning to arrive by public transport, you can catch a train to York, which has direct trains from London and Manchester, and connecting services around the country. You can then catch the 30, 30X, 31, or 31X bus service to Helmsley. To get home, you would need to catch a train from Filey Station back to York.

If you're planning to arrive by car, your best bet is to negotiate with a hotel or B&B a rate to stay for a night either side of your hike in Helmsley. Alternatively, you could book long-stay parking in York and catch the bus.

On The Map

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Cleveland Way

104 mi

10,525 ft

10,625 ft

Last updated: November 19, 2021

Tours & Highlights

  • Difficult
    08:38
    19.7 mi
    2.3 mph
    1,725 ft
    1,375 ft
    Expert Hiking Tour. Very good fitness required. Mostly accessible paths. Sure-footedness required.

    The first stage of the Cleveland Way is the perfect introduction to the trail. At almost 20 miles (32 km), this stage will push your fitness and endurance to the limit. (For details on how to split the hike, see below.)

    

    From Helmsley, you stroll east past Helmsley Castle and into Rye Valley, where the

    by Kit P

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  • Difficult
    06:20
    12.6 mi
    2.0 mph
    2,600 ft
    2,275 ft
    Expert Hiking Tour. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

    This stage voyages deep into Cleveland Hills and provides breathtaking views across Teesside and North Yorkshire.

    

    From Osmotherley, the trail heads north and passes within half-a-mile of Mount Grace Priory, the best-preserved Carthusian monastery in England. Whilst the detour to see Mount Grace will require

    by Kit P

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  • Difficult
    08:59
    19.6 mi
    2.2 mph
    2,075 ft
    2,550 ft
    Expert Hiking Tour. Very good fitness required. Mostly accessible paths. Sure-footedness required.

    This epic stage takes you to the highest point on the North York Moors and deep into Captain Cook country.

    

    With a challenging terrain and nearly 20 miles (32 km) of distance to contend with, this stage will be a real test of your mettle. (For details on how to split the hike, see below.)

    

    From Clay Bank

    by Kit P

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  • Difficult
    06:04
    13.5 mi
    2.2 mph
    1,275 ft
    1,625 ft
    Expert Hiking Tour. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

    Coastal views, hidden bays, smugglers coves and picturesque fishing villages await as the trail takes you along the Yorkshire Heritage Coastline.

    

    From Guisborough, you head northeast over farmland to Skelton and then follow the beck into the delightful coastal town of Saltburn by the Sea.

    

    It's worth taking

    by Kit P

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  • Difficult
    08:17
    18.8 mi
    2.3 mph
    1,575 ft
    1,575 ft
    Expert Hiking Tour. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

    This highlight-filled hike explores one of England’s most-celebrated stretches of coastline.

    

    At nearly 20 miles (32 km) long and with a tough terrain to contend with, this stage is a fantastic challenge. (For details on how to split the hike, see below.)

    

    From Staithes, climb over Beacon Hill and follow

    by Kit P

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  • Difficult
    06:08
    13.8 mi
    2.3 mph
    1,150 ft
    1,200 ft
    Expert Hiking Tour. Very good fitness required. Mostly accessible paths. Sure-footedness required.

    This stage explores cliffs and coves on a magnificent stretch of Yorkshire coastline.

    

    With superb views over land and sea for the entire hike, you finish in another much-loved seaside destination, Scarborough.

    

    From Robin Hood's Bay, you ascend over Ravenscar; gradually at first and becoming more intense

    by Kit P

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  • Intermediate
    04:29
    10.1 mi
    2.3 mph
    925 ft
    850 ft
    Intermediate Hiking Tour. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

    The final stage of the Cleveland Way takes you along charming coastal cliffs to the Victorian seaside resort of Filey.

    

    Before you leave Scarborough though, it's worth exploring the town a little. Some unmissable spots include Peasholm Park, a serene oriental-themed public space in a glen; and, of course

    by Kit P

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Collection Stats

  • Tours
    7
  • Distance
    108 mi
  • Duration
    48:56 h
  • Elevation
    11,300 ft

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Hike empty hills, majestic moors and golden coast — Cleveland Way

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