The Cleveland Way Guided Trail

Guided Trail


Print page

Activity types:

  • Coastal
  • Hills & moorland


  • 5
More information

Choosing the level of your walks

Our easy grading system shows whether a region offer gentle strolls or more challenging routes to help you choose the right holiday for you. Difficulty is measured on many factors such as distance, ascent/descent, terrain, weather and more. There's no magic formula, but from our experience we grade our walks 1 to 5 (where 1 is easy and 5 hard). Our challenger holidays require a high level of fitness and stamina.

More about difficulty levels

Holiday overview

Download the Cleveland Way Trip Notes 2019

The Cleveland Way National Trail is a 109 mile (175 Km) walk through the ever-changing scenery of the North Yorkshire Moors. Starting at Helmsley it follows a horseshoe around the beautiful North York Moors National Park crossing vibrant heather moorland, to join the coast at Saltburn. The Way then follows the dramatic coastline to Filey, passing old fishing villages and coastal towns.



Whitby with awards

Whitby is truly unique. Venture into this tight and twisty town whilst exploring the local architecture. Larpool Hall provides excellent accommodation and spacious public rooms. A magnificent location situated above the harbour and perfect for our walking and leisure activity holidays.

Larpool Hall has 28 newly refurbished bedrooms in the main building. Rooms at the front of the house enjoy wonderful views across the Esk Valley.


Whitby Good Accom Promo'Good' Rooms 

These rooms are all ensuite and furnished to a good standard. They include:

  • Check in from 2:30pm
  • Tea and coffee-making facilities
  • 23 inch TV
  • Toiletries
  • Hairdryer
  • Free WiFi

Whitby Better Accom Promo'Better' Rooms 

These rooms are slightly larger and/or have a better view. They include:

  • Early check in from 1pm
  • Tea & Coffee making facilities
  • Fluffy bathrobe & slippers
  • 32 inch TV
  • More luxurious mattress
  • Enhanced toiletries
  • Hairdryer
  • Smalls drying rack
  • Free WiFi

Only an extra £15 per person per night

Whitby Best Accom Promo'Best' Rooms 

These rooms truly are the best in the house for extra luxury during your stay. They include:

  • Recently refurbished to an exceptional standard
  • Large rooms
  • Stunning views of the surrounding area
  • Early check in from 1pm
  • Tea & Coffee making facilities
  • Fluffy bathrobe & slippers
  • 32 inch TV
  • More luxurious mattress
  • Enhanced toiletries
  • Hairdryer
  • Smalls drying rack
  • Free WiFi

Only an extra £20 per person per night

Choose Your Room: Our new “Choose Your Room” service is available at our UK country houses, providing the option to choose and confirm a specific room for an extra £30 per room. Supplements to upgrade to 'Better' or 'Best' rooms still apply. The choice of room number must be of the same room type as originally booked and is subject to availability.

At the house

  • Excellent boot and drying rooms
  • Lounge with a central dance floor
  • Two additional lounges
  • Bar
  • Outside terrace
  • Dining room
  • Range of board games and books
  • Free WiFi available in public rooms
  • Extension views from the front of the house across the esk Valley
  • Gardens include a putting green and croquet lawn


An example of Whitby chocolate fudge cake an option for dessertAll holidays at our Country Houses are full board accommodation including an evening meal on arrival to breakfast on the day of your departure. All of our Country Houses have a well-stocked bar serving local beers, wine and spirits.

Start your day with our extensive breakfast.
 Take your fill from our famous self-service picnic lunches
A relaxed social dinner is a highlight of any stay at our Country Houses

Your evenings

Make the most of your evening or join us at the barJust relax and take it easy, or if you'd like to continue to chat with our guides and fellow guests then why not grab a drink or take part in one of our optional evening activities.

All of our bars are stocked with locally sourced drinks so you can really soak up your surroundings.


Larpool Hall is accessible to wheelchair users

More details on Whitby accessibility

Additional information

  • Fire procedure is displayed in each room and explained to guests on arrival. Guests requiring assistance at an evacuation are identified at this time and door hanger cards are issued
  • Mobile phone reception is generally good from the main building
  • Assistance dogs accompanying visually or hearing impaired guests are welcome; dogs must be kept on a lead or harness at all times
  • Information can be provided in large print
  • Staff have received disability awareness training
  • Special diets can be catered for. Specialist food can be obtained with prior notice
  • Hired equipment can be arranged for your stay with prior notice
  • Fridge for medication can be supplied


Download the Cleveland Way Trip Notes 2019

Day 1: Arrival Day

Your leader will give an introductory talk about the holiday.

 Day 2: Helmsley to Osmotherley

Sutton Bank with a view over the Vale of YorkWe leave the delightful market town of Helmsley, passing the ruins of Rievaulx Abbey, set within the beautiful backdrop of the wooded Rye Valley. 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. 21.5 Miles (34.5 km) Ascent minimal.

 Day 3: Osmotherley to Kildale

Coast to coast Urra MoorShortly 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 1489 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 Blowarth 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 Kildale. 20.5 miles (33 km) Ascent 3200 ft (960 m).

 Day 4: Kildale to Skinningrove

Roseberry ToppingLeaving Kildale we cross the Esk Valley Railway, one of the few surviving "country" lines. We ascend to 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 320m (1050 feet) 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. 17½ miles (28km), with 1,700 feet (510m) of ascent; with Roseberry Topping option, 18½ miles (30km), with 2,150 feet (645m) of ascent.

 Day 5: Skinningrove to Whitby

View along the coast from Boulby CliffBeyond Skinningrove we ascend to the dramatic cliffs of Boulby, the highest on the eastern coast of England at 203 metres (666 feet). 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. 17.5 miles (28 km) 1550 ft (465 m).

 Day 6: Whitby to Cloughton Wyke

View along the coast to Robin Hood's BayWe leave Whitby by ascending the 199 steps up 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 3600 feet (1090m) ascent.

 Day 7: Cloughton Wyke to Filey Brigg

Scarborough Castle on the Cleveland WayThe 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 (23 km) with 2000 feet (630m) ascent.

Day 8: Departure day

The itinerary may be subject to change at the discretion of the leader with regard to the weather and other external factors.

Local area

Discover the North York Moors

During your stay at Larpool Hall you may enjoy visiting the following places of interest, either in your free time, or on your journey to and from Whitby:     

Whitby is a bustling harbour town and a popular tourist destination. From Larpool Hall it is a 1½ miles downhill walk, or a short drive to the town centre. The town has a full range of facilities including shops, banks, pubs and cafés. If you don’t mind the queue, the Magpie café on the waterfront is said to serve England’s best fish and chips!

Ruined stone walls of Whitby AbbeyWhitby Abbey               
The iconic ruined abbey commands a wonderful position above the harbour and can be reached by climbing the famous 199 steps. About 10 minutes' drive or a 1½ mile walk.



Old houses and harbour at StaithesStaithes            
The pretty fishing village of Staithes is a pleasant spot to visit. Young children may well recognise the village as the setting for Old Jacks Boat on CBeebies. Around 25 minutes' drive from Whitby.



Steam train in the North York MoorsNorth Yorkshire Moors Railway               
The North Yorkshire Moors Railway operates steam trains over its 18 mile line between Grosmont and Pickering and in the summer some trains continue over the British Rail branch line to Whitby. This is a highly scenic route: one reason why the line has become Britain’s most visited steam railway. The well-kept and historic stations are worth seeing for their own sake and you may well recognise Goathland which has doubled as ‘Adensfield’ on the Heartbeat TV series, and as ‘Hogsmeade’ in the Harry Potter films. Either join the train at Whitby, or at Grosmont, about 20 minutes' drive away.

Scarborough & Stephen Joseph Theatre
Scarborough is a quintessential Victorian seaside resort with plenty of attractions for both young and old. The Stephen Joseph Theatre in Scarborough is home to Alan Ayckbourn, the renowned playwright. It has two theatres - the round and the McCarthy which doubles as a cinema, plus a restaurant and shop.

Whitby to Scarborough Cycle Trail
This superb trail uses the route of disused railway line and offers miles of traffic-free cycling, often with outstanding sea views. The trail passes right next to Larpool Hall and heads south  to Robin Hoods Bay, Ravenscar, or if you are feeling keen to Scarborough. Bikes can be hired at nearby Hawsker.

Rydale Folk Museum
This museum is located at Hutton-Le-Hole, about 50 minutes' drive from Whitby. This pretty village west of Pickering that has a feel of a Cotswold village, being built of mellow stone and with a stream though the middle. The museum houses exhaustive displays of rural life and crafts in buildings spread over several acres.

Fountain and extrerior of Castle Howard houseCastle Howard
Located near Malton about an hour's drive from Whitby, Castle Howard is one of Britain’s grandest stately homes. It is well known as the location for the TV series Brideshead Revisited. Today the house is still owned by the Howard family and the building hosts many exhibitions & events throughout the year. Also of interest are the extensive gardens that contain a formal rose garden and elegant ponds and fountains.


Blue Mallard locomotive at National Railway MuseumYork
One of Britain’s most attractive historic cities, York is about a 1 hour 20 minutes drive from Larpool Hall. Attractions include the city walls, Minster, National Railway Museum, and Yorvik Viking Centre. or



Travel to Whitby

Our address is: Larpool Hall, Larpool Drive, Whitby, North Yorkshire, YO22 4ND

How to get to us by train

By train:

The nearest railway station to Larpool Hall is at Whitby, However, you may find that travelling to Scarborough station is more convenient.  For train times and route planning by train visit or phone 03457 48 49 50.

Get to us by Taxi

By taxi:

The 2 mile journey from Whitby station takes approximately 10 minutes, with a cost of around £6 per 4 seat taxi. The 21 mile journey from Scarborough rail station takes approximately 40 minutes, with a cost of around £30 per 4 seat taxi. Details of our current recommended taxi company and rates will be sent to you with your booking. The return taxi journey can be arranged on your behalf by the Larpool Hall Manager.


By bus:

The 93 bus runs regularly between Scarborough station and Whitby. As you approach Whitby, alight by the Larpool Industrial Estate. From here it is an 800 metre walk to Larpool Hall. See for bus times.

Driving to us

By car:

Most guests approach Whitby via the A171 from Teesside or the A169 from Pickering and Malton; these roads converge at a roundabout about 2 miles outside Whitby. After this roundabout and as you approach Whitby, cross another roundabout then turn right at the traffic lights signposted to Scarborough. Cross the large bridge over the River Esk, then immediately turn right into Larpool Lane. Towards the top of the hill take the narrowing road of Larpool Drive. Larpool Hall is directly ahead at the end of this road. A free car park is available in the grounds.

 Travel by plane

Travelling from overseas

Manchester Airport is served by a range of long-haul flights. There are trains every hour from the airport to Scarborough with one change at Manchester Piccadilly. Allow 2hrs 50 minutes to Scarborough - see for train times.

Flying to London Heathrow airport is another option, but has a longer onward train journey - allow 4½ hours to reach Scarborough. From Heathrow first take the Piccadilly line Underground train to London Kings Cross station. From here take a train to Scarborough (1 change at York) - see for train times.

From Scarborough you can complete the journey to Whitby by bus or taxi (see above).


Dates & Prices

We're sorry, there are no dates available for this holiday at the moment. Please check out our other tours and breaks or call our team on 0345 470 8558 to be notified of new dates as soon as they become available.

Prices are per person

Sign up for our newsletter

Our newsletters are a great way to receive special offers, inspiring articles, stories and news from HF Holidays.

To subscribe, please enter your email address below and click 'submit'.

We won't pass your details on to any third party unless we have your express permission, you are free to unsubscribe at any time.