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

Hiking Collection by
komoot

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

The 109 mile (175 kilometer) 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 affords 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 stood 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, which can also be observed.

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, we complete the Cleveland Way in 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 kilometers)—we have suggestions on how to split these routes, which makes for a leisurely ten day itinerary.

Of course, you can split up each stage into as many days as you are 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 is worth planning in advance and scheduling any rest days accordingly. Campers are relatively well-served along the route.

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

If you are 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 follow the bus instructions above.

For more information about the Cleveland Way, visit: nationaltrail.co.uk/cleveland-way.
For train timetables and tickets, visit: thetrainline.com.
For the 30 30X 31 31X bus timetable, visit: yorkbus.co.uk/cmsUploads/route/files/3030X3131XWEBAPR18.pdf.

On The Map

Tours & Highlights

  • Difficult
    08:41
    19.8 mi
    2.3 mph
    1,700 ft
    1,350 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 kilometers), 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 breathtaking Rievaulx Abbey comes into focus.

    You cross the river at Rievaulx Bridge and continue through farmland and woodland, passing the villages of Cold Kirkby and Sutton Bank.

    The trail ascends through Garbutt Wood Nature Reserve and then opens up onto Whitestone cliff, where you are afforded spectacular views over Gormire Lake and beyond.

    You continue along the Hambleton Hills and onto Arden Great Moor before dropping into the village of Osmotherley.

    Osmotherley, where this stage finishes, has a good range of accommodation and places to eat and drink.

    If you want to split this hike, try ending stage one at Sutton Bank Visitor Centre. From there, you can organize transport to Old Thirsk, which has plenty of accommodation. This hike is around nine miles (14.4 kilometers).

    The following day, pick the trail back up at Sutton Bank and hike the remaining 11 miles (18 kilometers) to Osmotherley.

  • Difficult
    06:46
    13.6 mi
    2.0 mph
    2,725 ft
    2,400 ft
    Expert Hiking Tour. Very good fitness required. Mostly accessible paths. Sure-footedness required.

    This stage voyages deep into Cleveland Hills and affords 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 you to lose height—and put it back on again—it is worth the effort.

    From here, the rugged charm of Cleveland Hills is plain to see. This next section crosses five moors: Scarth Wood Moor, Live Moor, Cringle Moor, Cold Moor and Hasty Bank.

    The final ascent gets you to The Wainstones; a fierce-looking rocky outcrop with fantastic views over Middlesbrough and the Tees.

    You then descend to Clay Bank, where this stage finishes. Here, you will need to follow the road north for around two-and-a-half miles (four kilometers) to Great Broughton, which has accommodation and food and drink options.

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  • Difficult
    08:54
    19.5 mi
    2.2 mph
    2,025 ft
    2,475 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 kilometers) 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, you climb onto the vast expanse of Urra Moor and soon arrive at the highest point in the national park, Round Hill, which stands at 1,490 feet (454 meters).

    The moorland is bleak and lonely along this next section, albeit with a tranquil charm.

    You then drop into the village of Kildale before ascending to Captain Cook's Monument. At the 1,063 feet (324 meter) summit of Easby Moor, the monument to this legendary captain affords breathtaking views over the landscape.

    From Easby Moor you can see the distinctive shape of Roseberry Topping in the distance. The short, yet challenging climb to the summit of the hill is lots of fun, affords breathtaking views, and is a worthy detour.

    If you do not climb Roseberry Topping, it will shorten this stage by one mile (two kilometers) and will save a lot of effort.

    From there you descend to Slapewath and follow the road north to the market town of Guisborough, which has a good range of accommodation and places to eat and drink.

    If you want to split this stage, try descending to Great Ayton after seeing the Captain Cook monument to finish. The village has a decent range of accommodation and places to eat and drink.

    This will roughly split this stage into one 12 mile (19 kilometer) hike, followed by a seven-and-a-half mile (12 kilometer) hike to Guisborough.

  • Difficult
    06:11
    13.7 mi
    2.2 mph
    1,275 ft
    1,650 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 is worth taking some time to explore Saltburn. The Victorian beach resort has a glorious echo of the past and is surrounded by dramatic cliffs. There is a thriving art scene in the town and lots of places to stop for lunch, too.

    The trail then follows coastal cliffs above Cattersty Sands and continues to Staithes, a sleepy fishing village with lots of charm.

    As you wander through the winding streets of Staithes to the traditional bay, it might feel like time has stood still for hundreds of years.

    Staithes has a good range of accommodation, places to eat and drink, as well as shops and other attractions.

  • Difficult
    08:50
    20.0 mi
    2.3 mph
    1,675 ft
    1,650 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 kilometers) long and with a tough terrain to contend with, this stage will really test your fitness and stamina. (For details on how to split the hike, see below.)

    From Staithes, climb over Beacon Hill and follow the cliffs to Runswick Bay, one of the prettiest coastal destinations in Yorkshire.

    With a sweeping and sheltered bay, sandy beach, clean water, and interesting rock pools, Runswick is a wonderful place for relaxation and exploration.

    You continue along the cliffs past Sandsend Beach, which ultimately turns into Whitby Beach.

    With cobbled streets winding past old inns and taverns, a bustling harbor, the striking ruins of Whitby Abbey, and connections to Captain Cook and Dracula, Whitby is well worth exploring.

    After leaving the hustle-and-bustle behind, you return to the coastal cliffs for solitude, reinvigorating winds, and glorious views all the way to Robin Hood’s Bay, which is a wonderful place to end this stage.

    With a sandy beach and clean sea, Robin Hood’s Bay is an enchanting labyrinth of cobbled streets, quirky taverns, and postcard cottages, surrounded by spectacular countryside.

    Robin Hood’s Bay has a good range of accommodation, places to eat and drink, as well as shops and other attractions.

    The easiest way to split this stage is to spend a night in Whitby, which has a good range of accommodation and places to eat and drink.

    From Staithes to Whitby is 12 miles (19 kilometers). The following stage, from Whitby to Robin Hood’s Bay would then be eight miles (13 kilometers).

  • Difficult
    06:15
    14.1 mi
    2.3 mph
    1,125 ft
    1,175 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 to finish.

    You will see the evidence of a bygone industrial age all around you along this coastline. Peak Alum Works, which quarried Alum for textiles in the 16th century, is a good example that you pass.

    The trail descends gradually to Hayburn Wyke, climbs over Cober Hill, and then stays level all the way to Scarborough.

    As you enter the town, the inviting sand and sea of North Bay might tempt you. Also, be sure to check out the giant steel statue on a giant bench, Freddie Gilroy and the Belsen Stragglers.

    Scarborough has a good range of accommodation, places to eat and drink, as well as shops and other attractions.

  • Difficult
    05:12
    11.8 mi
    2.3 mph
    1,025 ft
    950 ft
    Expert Hiking Tour. Very 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 is worth exploring the town a little. Some unmissable spots include North Bay, an inviting Blue Flag beach; Peasholm Park, a serene oriental-themed public space in a glen; and, of course, Scarborough Castle.

    Sat high on a rocky outcrop, the site of Scarborough Castle has been inhabited as a natural fortress for nearly 3,000 years. From the castle, you are afforded breathtaking views over the town, the surrounding landscape, and out to sea.

    From Scarborough, you will walk past the former location of the Holbeck Hall Hotel, which famously slipped into the sea in front of the British media in 1994.

    The trail continues over Cayton Bay, past Castle Rocks, Casty Rocks, and Old Horse Rocks, all the while with superb views, to the serene coastal town of Filey.

    Filey marks the end of this stage and the end of the Cleveland Way. The town has a good range of accommodation, places to eat and drink, as well as shops and other attractions.

Collection Stats

  • Tours
    7
  • Distance
    113 mi
  • Duration
    50:50 h
  • Elevation
    11,550 ft11,675 ft

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