The Cleveland Way Complete Guided Trail

The Cleveland Way Guided Trail

Views from the Cleveland Way, North York Moors, UK.
Duration: 7 nights
Type: Guided Trails
Walking Grade: 5
from £1,029pp £999pp

The Cleveland Way National Trail is a 109 mile (175 Km) walking route through the ever changing scenery of North Yorkshire. Starting at Helmsley, the Cleveland Way follows a horseshoe line around much of the beautiful North York Moors National Park, first heading across the inspirational and sometimes vibrant heather moorland, before reaching the coast at Saltburn. From here it’s a visual feast along the dramatic coastline to Filey, passing old fishing villages and lively coastal towns. Along the way we follow ancient trods, passing medieval crosses and a wealth of historical sites, Helmsley Castle, Rievaulx Abbey, Mount Grace Priory, Whitby Abbey and Scarborough Castle to name just a few. The second National Trail to be designated, the Cleveland Way was officially opened at Helmsley Youth Hostel in May 1969.

Holiday Highlights

  • Hike the 109 mile (175 Km) walk through the ever-changing scenery of the North Yorkshire Moors.
  • Follow a 'horseshoe' around the beautiful North York Moors National Park
  • Walk the dramatic coastline to Filey, passing old fishing villages and coastal towns
  • View the iconic ruins of Whitby and Rievaulx Abbeys

What’s included

  • High quality en-suite accommodation in our country house
  • Full board from dinner upon arrival to breakfast on departure day
  • The services of an HF Holidays' walks leader
  • All transport on walking days

Trip Notes

Trip notes are detailed, downloadable PDF’s for each holiday, please click the button below to find the right trip notes for your departure date.

109 miles with 15-22 miles and up to 3,750 feet of ascent in a day

You're welcome to check in from 4pm onwards.

Enjoy a complimentary Afternoon Tea on arrival.

We leave the delightful market town of Helmsley, passing the ruins of Rievaulx Abbey, set within the beautiful backdrop of the wooded Ryedale. Walking through the woodlands of Nettledale, we reach the small village of Cold Kirby then pass Hambleton Down, once the site of a major racecourse. Arriving at Sutton Bank we can admire the spectacular view over the Vale of York. We continue along the limestone edge of the Hambleton Hills, catching a glimpse below of Gormire Lake, one of only three natural lakes in Yorkshire. We then follow the historic Hambleton Drove Road, used since prehistoric times but especially during 18th and 19th centuries when Scottish cattlemen drove their herds down to market towns in England. We descend from the moor past the reservoir at Oakdale towards the attractive village of Osmotherley.

19½ miles (31.5km) with 2,850 feet (875m) of ascent.

Shortly after leaving Osmotherley, we join the route of the Lyke Wake Walk, which runs for 42 miles east to the coast at Ravenscar. Our rollercoaster path follows the northern escarpment of the North York Moors National Park, with outstanding views both north across the Vale of York and south and east into the moors. We will see signs of alum, jet and ironstone mining, reminders of the industrial past. We visit the massive sandstone blocks known as the Wainstones, before crossing the road at Hasty Bank to ascend Urra Moor to Round Hill, at 1,489 feet (454m) the highest point on the moor. Beside the trail we look out for moorland stone markers - the handstone marked an ancient route between Stokesley and Kirkbymoorside. The remotest point of the entire Cleveland Way is at Bloworth Crossing, once part of a busy mineral line bringing ironstone out of Rosedale to serve the developing industries of Teesside. Here we leave the Lyke Wake Walk, heading north again to drop down into Kildale.

20½ miles (33km) with 3,750 feet (1150m) of ascent.

Leaving Kildale we cross the Esk Valley Railway, one of the few surviving "country" lines. We ascend Easby Moor to Captain Cook’s Monument, an impressive obelisk erected in 1827. From here the iconic Roseberry Topping comes into sight - the reward for reaching its 1,050 feet (320m) summit are outstanding views on all sides. Heading east we reach Highcliff Nab and continue through Guisborough Woods to leave the moors at Slapewath, passing through Skelton and a delightful wooded valley to reach the coast at Saltburn, a Victorian resort with a long stretch of sandy beach. We then rise quickly onto the cliff top, passing the remains of a Roman Signal Station on Hunt Cliff and a number of industrial sculptures before descending to Skinningrove.

17 miles (27.5km), with 2,500 feet (770m) of ascent; with Roseberry Topping option, 18 miles (29km) with 2,950 feet (900m) of ascent.

Beyond Skinningrove we ascend to the dramatic cliffs of Boulby, the highest on the Eastern coast of England at 666 feet (203m). Once more we pass evidence of alum workings before reaching Boulby Potash mine, the deepest in Europe. We continue to Staithes, with its picturesque harbour, narrow alleyways and cluster of red roofed houses. Another stretch of cliff path brings us to Runswick Bay where we can walk along the beach before going up onto the cliffs once more. Passing Kettleness, we are reminded of the ever-present nature of coastal erosion - the original village slipped into the sea in 1829. Our journey continues along the old railway line to Sandsend where we may be able to walk along the beach to Whitby.

17½ miles (28 km) with 2,100 feet (650m) of ascent.

We leave Whitby by ascending the 199 steps to St Mary’s church, where the classic outline of Whitby Abbey comes into view. A pleasant walk along the cliff top brings us to Robin Hoods Bay, which marks the end of the Coast to Coast walk. The shore here is rich in fossils, the cliffs interrupted at Boggle Hole and Stoupe Beck. From here we ascend gently, passing through the extensive former alum works, considered one of the earliest sites of chemical industry. At Ravenscar we can learn about the “Town that never was”. From Ravenscar the trail continues along more wooded cliffs, dropping into the delightful wooded bay of Hayburn Wyke. We continue to Cloughton Wyke.

17 miles (27km) with 3,100 feet (955m) ascent.

The cliffs beyond Cloughton Wyke are lower, and soon Scarborough Castle comes into view. We continue towards this busy seaside resort, where there’ll be time for refreshments as we pass through the largest town on our route. As we leave Scarborough, we will see the former location of the Holbeck Hall Hotel, which famously slipped into the sea in 1994. Some of the bungalows at Knipe Point have also been lost to the sea in recent years. The walk passes above the beautiful expanse of Cayton Bay before you enjoy the last few miles through to the stunning geographical location of Filey Brigg, a birdwatchers’ paradise and fitting end to our journey.

15 miles (24 km) with 2,000 feet (630m) ascent.

Enjoy a leisurely breakfast before making your way home.

Cleveland Way Map new

Larpool Hall

Escape to Whitby, whose handsome harbour and medieval streets are famously the setting for Bram Stoker’s Dracula and home to the world’s best fish and chips, for a stay in Larpool Hall. This imposing Grade II listed Georgian mansion has been part of the town for hundreds of years and has evolved to offer an updated take on traditional hospitality. The Hall retains its original grandeur and styling, while offering guests the perfect mix of contemporary comforts to deliver a large amount of atmosphere and character. Sweep up the magnificent staircase, marvel at the impressive fireplaces, watch through the large picture windows and feel yourself transported. With 29 rooms, 14 acres of attractive grounds and views over the Esk Valley, you couldn’t be better placed. Step out to explore the coast, Captain Cook country or walk on the Cleveland Way. Discover Robin Hood’s Bay and hunt for fossils or head deep into the North York Moors for a contrasting landscape carpeted in sweetly scented heather.



Tea & coffee-making facilities, TV, Hairdryer, Toiletries, Wi-Fi

Stay in one of the Hall’s smartly presented rooms, where contemporary design touches complement the original architecture and features. With 29 bedrooms, Larpool Hall has plenty of space and there’s a range of Classic, Premium and Superior Rooms to choose from. Choose the very spacious Room 15 on the ground floor for its lemon and grey styling, super-comfy sofa in front of a large fireplace and views across the Esk Valley. Climb to Room 2 on the first floor for similarly expansive vistas from the front of the house, or settle in under the eaves and exposed beams of beautiful Room 30 on the second floor of the house.

All ‘Classic’ rooms are ensuite and furnished to a high standard. There are also several ‘Premium’ and ‘Superior' Rooms that are either larger or have a desirable view, a more luxurious mattress and larger television – upgrade your stay for just an extra £15-25 per person per night. You can choose a specific room for an extra £30 per room, subject to availability. Upgrade supplements still apply.


Free Wi-Fi, boot room and drying room, extensive garden, multi-purpose activity room, three lounges, library and board games to borrow

After a day exploring the tight and twisty streets of Whitby or the windswept headlands and smugglers’ haunts of the Yorkshire coast, come back to the house and its specially tailored walkers’ facilities. Relax outside in the pretty courtyard or stroll the 14 acres of grounds and gardens with their manicured lawns and mature trees. Grab a well-thumbed copy of Dracula and hole up in the lounge, or join fellow guests in the large ballroom with its comfy seating and central dance floor to discuss your own adventures. The small, sociable bar provides another great space in which to relax.

Food & Drink

As at all our country houses, holidays are full board, from afternoon tea served as a welcome treat through that evening’s meal to a hearty breakfast on the day of departure. Food at Larpool Hall is varied with a strong emphasis on the use of seasonal British produce. Our experienced chefs create each dish using only the freshest ingredients and, when in season, use home grown herbs and vegetables taken from our own gardens to give a true taste of the local area.


For accessibility and assistance information, please contact our expert team on 020 3974 8865 or view the accessibility information online for Larpool Hall

10674_0050 - Larpool Hall - Exterior

Getting to Larpool Hall

Find out more about this location including travel details and room types.

More Information

Essential Information

“There’s no such thing as bad weather, just the wrong type of clothing!” goes the adage. Come prepared for all eventualities and you’ll walk in comfort as well as safety. Britain’s famous for its changeable weather, so here’s our advice on what to wear and bring.


  • Waterproof walking boots providing ankle support and good grip.
  • A waterproof jacket and over-trousers
  • Gloves and a warm hat (it can be chilly at any time of the year)
  • Rucksack
  • Water bottle (at least 1 litre capacity)
  • A small torch (everywhere in winter, year round in mountains)
  • Sun hat and sunscreen
    Denim jeans and waterproof capes are not suitable on any walks.


  • Several layers of clothing, which can be added or removed
  • Specialist walking socks to avoid blisters.
  • A first aid kit inc plasters– your leader’s first aid kit doesn’t contain any medication
  • Sit mat (insulated pad to sit on when you stop for a break)

You might also want

  • Walking poles, particularly useful for descents.
  • Insect repellent
  • Flask for hot drinks
  • Rigid lunch box
  • Gaiters
  • Blister kit (eg Compeed) just in case
  • Waterproof rucksack liner

Guest Reviews

All holidays are subject to availability. Prices are subject to change.
Prices based on two people sharing. Supplements may apply.
Non-member fee: £30 per person.

Holiday Prices

Date (Start - End) Nights Itinerary Price Status Trip Notes Book
15 Jul - 22 Jul 2022
7 Guided Trail £1,029 Trip Notes Book Now
02 Sep - 09 Sep 2022
7 Guided Trail £1,029 £999 Save £30 Per Person Trip Notes Book Now
7 nights
Guided Trails
Walking Grade:

7 nights from £1,029pp £999pp

...or call 020 3974 8865

For group bookings of 10+ people click here

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