The Cleveland Way Guided Trail

Views from the Cleveland Way, North York Moors, UK.
Duration: 7 nights
Type: Guided trails
Walking Grade: 5

Walks in the North York Moors National Park don’t get better than the Cleveland Way. This 109-mile-long trail winds its way through the ever-changing scenery of North Yorkshire from the charming market town of Helmsley to the lively seaside resort of Filey. Cross heather-clad moorland and follow dramatic stretches of coastline where highlights include the ruins of 12th century Rievaulx Abbey, Whitby Abbey, Captain Cook’s Monument, and the villages of Great Ayton and Robin Hood’s Bay.

What you’ll love

  • Conquering all 109 miles of the Cleveland Way
  • Exploring the best of the North York Moors National Park
  • Walking over wild moorland and along dramatic coastline
  • Visiting the iconic ruins of Whitby Abbey
  • Soaking up views from Roseberry Topping
  • Spending time in Robin Hood's Bay

What’s included

  • Comfortable en-suite rooms in our partner accommodation(s)
  • Cooked or continental breakfast every morning
  • Daily packed lunches
  • Three-course evening meals, plus tea & coffee
  • Guided walks with an experienced HF Holidays Leader
  • All transport to and from walks where necessary 

Trip Notes

Easy to download as a PDF, our trip notes provide detailed information for every holiday. Please click below to find the trip notes for your departure date.

All our carefully-curated itineraries are designed by our experts. While we make every effort to adhere to the described itinerary, we may take alternative routes or adapt the running order for weather and/or operational reasons.

You're welcome to check in from 4pm onwards. Enjoy a complimentary cream 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 2,450 feet (740m) 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 3,600 feet (1,100m) 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.

18 miles (28.5km), with 2,250 feet (680m) of ascent; with Roseberry Topping option, 19 miles (30.5km) with 2,700 feet (820m) 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.

18 miles (29 km) with 2,800 feet (860m) 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.

18 miles (29km) with 2,650 feet (800m) 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.

15½ miles (25 km) with 1,700 feet (520m) ascent.

Enjoy a leisurely breakfast before making your way home.

Itinerary map for Cleveland Way

Larpool Hall

Given that the Yorkshire coast never loses its capacity to enchant, it’s easy to see the appeal of this Grade II-listed house overlooking the Esk Valley and the North Sea. The setting is perfect; in the former fishing town of Whitby that’s best known for its fish and chips, quaint harbour, and Dracula connections (Irish author Bram Stoker drew his inspiration for his Gothic novel when holidaying here in 1890). You’ll have all the sightseeing greats within walking or driving distance, including the 13th century Whitby Abbey, the wonderful Whitby Sands, and the 199 Steps leading up to the old St. Mary’s Church (it’s customary to count them as you climb). Not only are the North York Moors right on your doorstep, but the walk along Cleveland Way to Robin Hood’s Bay is rather special, too.   



Designed with your comfort in mind, Larpool Hall has 29 well-appointed guest rooms available in three categories: Classic, Premium, and Superior. 

Classic Rooms are comfortable en-suite guest rooms, ideal for a peaceful night's sleep. Amenities include free Wi-Fi, tea and coffee-making facilities, toiletries (hand wash, shampoo, and shower gel), and a TV. 

Premium Rooms are more spacious en-suite guest rooms. Amenities include free Wi-Fi, tea and coffee-making facilities, toiletries (hand wash, shampoo, body lotion, shower gel), and a 32-inch TV. Extras include bathrobes, slippers, and comfortable mattresses.

Superior Rooms are even more spacious en-suite guest rooms offering upgraded views of the surrounds. Amenities include free Wi-Fi, tea and coffee-making facilities, toiletries (hand wash, shampoo, body lotion, shower gel), and a 32-inch TV. Extras include bathrobes, slippers, and comfortable mattresses.

We love: The spacious Room 15 on the ground floor for its lovely décor, comfy sofa, large fireplace, and views across the Esk Valley. Room 2 on the first floor offers fabulous views while Room 30 on the second floor has eaves and exposed beams. 

The Choose Your Room service is available at our UK country houses, allowing you the option of choosing and confirming a specific room for an extra charge of £30 per room. This is subject to availability. Upgrade supplements apply. 

Check in & check out
You are welcome to check in from 4:00pm at the earliest. On arrival, you’ll enjoy a complimentary cream tea and get to meet your fellow guests, our HF Holidays Leaders, and the rest of the friendly team.  

On the day of departure, we kindly ask all guests to check out by 10:00am. You’ll be asked to settle your bill prior to leaving. You may, of course, make a charitable donation to our HF Holidays Pathways Fund if you wish. Please note that we only accept card payments.  

Room supplements

Superior Premium single Premium double/twin Choose your room
£25 pppn £20 pppn £20 pppn £30 per room

About your stay

A warm welcome
We want you to feel comfortable from the moment you arrive. You’ll find a welcome pack in your room with guest registration forms, menus, order forms for dinners and picnic lunches, the Wi-Fi password, and the front door code. Our houses are locked at night, so we recommend noting the Duty Manager’s number on arrival in case of an emergency (or getting locked out). 

Evening entertainment
While evening entertainment varies from house to house, the HF Holidays Big Pub Quiz held after dinner on Wednesdays is a weekly staple. Your HF Holidays Leader may be around for tips on guided and self-guided walking routes as well as visit-worthy local attractions. 

Walks talks 
Our HF Holidays Leaders host guided walking information briefings before dinner on arrival days. This is followed by a group Walks Talk for information on the following day’s walking delights (held before dinner every evening). Self-guided walking guests are, of course, welcome.  

The walking day
Prior to setting off on walks, your HF Holidays Leader will run you through a short safety briefing. There’s also an up-to-date weather forecast on display at the house to ensure you have appropriate clothing and footwear. If you choose to do your own walks or are on a self-guided walking holiday, we ask that you please complete an Independent Walker Card each day. These can be found near the Discovery Point in the house. 

Food & drink

Led by experienced chefs, we serve a wide range of dishes made with fresh and seasonal ingredients. We always aim to source the best produce available and use home-grown herbs and vegetables from our own gardens whenever possible. Additionally, we have a licensed bar with beers, soft drinks, and a superb selection of spirits. Full-board comes as standard and includes a cream tea on arrival and a hearty breakfast on departure day.

HF Holidays understands the importance of managing allergens effectively to ensure food is safe for guests with food allergies. Whilst we are always able to confidently inform guests which allergens are present in our ingredients and dishes, we are unable to guarantee absolute freedom from the 14 main allergens in our kitchens. Vegetarian and vegan menu choices are available. If you have allergies, food intolerances, or any special dietary requirements, please inform our reservation team at the time of booking.


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


Larpool Hall
Larpool Drive
North Yorkshire YO22 4ND

Tel: +44 (0)1947 602737

By train

The nearest station is Whitby. 

However, travelling to Scarborough station may be more convenient. Check National Rail for routes and journey times. 

By taxi

The two-mile journey from Whitby station takes approximately 10 minutes.  

From Scarborough train station, it’s a 21-mile journey, taking 40 minutes.  

For pricing, please contact Whitby Taxis directly.

Whitby Taxis
You can pre-book a taxi from our recommended company, Abbey Taxis*. We recommend booking your taxi at least seven days in advance by contacting:

Tel: +44 (0)1947 601212

A return journey can be arranged on your behalf by the HF Holidays House Manager at Larpool Hall.

*Whitby Taxis is not owned or managed by HF Holidays.

By bus

The 93 and 94 buses run regularly between Scarborough station and Whitby taking around an hour. As you approach Whitby, alight by the Larpool Lane Industrial Estate. From here it’s an 800m walk up Larpool Lane to Larpool Hall. Please note that Larpool Hall's driveway is not lit. 

Check Traveline for up-to-date bus information. 

By car

There’s a free car park at Larpool Hall if you decide to drive. 

The A171 from Teesside and the A169 from Pickering converge at a roundabout about two miles outside Whitby.  

After this roundabout and as you approach Whitby, cross another roundabout then turn right at the traffic lights signposted Scarborough. Cross over the River Esk, then immediately turn right into Larpool Lane. Towards the top of the hill, turn into Larpool Drive – you'll see Larpool Hall at the end of this road.  

By air

The nearest airport is Leeds Bradford Airport. 

Catch the airport bus to Leeds where there are connecting trains to Scarborough taking about 90 minutes.

There’s also Manchester Airport, which is served by a range of long-haul flights. From here, there are trains every hour to Scarborough with one change at Manchester Piccadilly or York. Allow around three hours to reach Scarborough. 

Flying to London Heathrow airport is another option but it’ll take you around 4.5 hours to reach Scarborough. From Heathrow first take the Piccadilly line to London Kings Cross station, then connect to Scarborough (with one change at York). 

Check National Rail for train information. 

The UK has a famously unpredictable climate so it's best to be prepared for weather that’s sunny one minute and raining the next.  To make it easier, here’s a list of items you should consider packing.   


  • Suitable footwear such as waterproof walking boots that provide ankle support and good grip  
  • Waterproof and windproof jacket 
  • Comfortable clothing (jeans & waterproof capes are not suitable)  
  • Mid-layer(s) to keep you warm. Fleeces make a good choice
  • Waterproof overtrousers  
  • Gloves and a warm hat  
  • Rucksack with waterproof liner 
  • Spotting scope and/or binoculars 
  • Flask for hot drinks   
  • Water bottle (at least 1 litre capacity)  
  • Sunscreen  
  • UV sunglasses  


  • Several base layers (long-sleeve or short-sleeve)  
  • Cushioned walking socks to avoid blisters  
  • First aid kit, including plasters and insect repellent 
  • Sit mat   
  • Waterproof pouch for valuables  
  • Rubbish bag (remember to always leave no trace)  
  • Wallet/purse  
  • Camera 
  • First-aid kit 

Larpool Hall Calendar

  • Guided Walking
  • Self-Guided Walking
  • Special Interests
  • Unavailable to Book

Guest reviews

7 nights
Guided trails
Walking Grade:

Call to Enquire

020 3974 8865

For group bookings of 10+ guests click here

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