6-Night North York Moors Outdoor Escapes Holiday

Scenic view of Whitby city in autumn sunny day
Duration: 6 nights
Type: Outdoor Escapes
Walking Grade: 3, 4 & 5

Brimming with coastal charm, Whitby welcomes you with its handsome harbour and medieval streets. Experience the very best of the North York Moors on our walks. Each day we'll offer three options, ranging from relaxing shorter strolls, to more challenging longer walks. Our flexible programme allows you to choose the option that suits your mood.

Holiday Highlights

When you visit the RNLI base in Staithes. We'll introduce you to one or two unsung heroes who provide a 24/7 emergency service on the local stretch of coastline. You can get the inside track on this local team - over the last 148 years lifeboats have been stationed at both Staithes and Runswick Bay and the crews have been presented with nine awards for gallantry - and gain a real insight into the people and the community here. 

Trip Notes

Trip notes are detailed, downloadable PDFs for each holiday.

Download Trip Notes

On our Guided Walking holidays, we believe that choice is key. Our walks descriptions will help you choose according to your interests and fitness. The walks are grouped together with care by local experts to give the best experience. While every effort will be made to adhere to the described itinerary, we may occasionally vary the sequence shown here or substitute an alternative route to suit local conditions or for other operational reasons, potentially at short notice.

Join us at our Larpool Hall Country House for an action-packed short break. If the weather is fine we can take a short pre-dinner stroll to the Larpool Viaduct to help get your bearings. After a delicious 3-course evening meal, there's time to relax with the rest of the group and look forward to the adventures to come. 

Discover the beautiful Cleveland Coast, on walks that take in the quaint fishing village of Staithes, and finish at Runswick Bay. 

Option 1 - Boulby to Runswick Bay

Distance: 6½ miles (10km) 

Ascent: 900 feet (280m) 

In Summary: Follow the Cleveland Way along the coast from Boulby cliff to Staithes and chat with members of the local RNLI down at the local lifeboat station. It's then along the cliffs to Port Musgrave and the sweeping arc of Runswick Bay. 

Highlight: Time to discover the fascinating fishing village of Staithes, and its Captain Cook connections. 


Option 2 - Skinningrove to Runswick Bay

Distance: 8 miles (13km) 

Ascent: 1,600 feet (480m) 

In Summary: A fantastic coastal walk starting from Skinningrove and heading to Boulby Cliff. Time to explore Staithes, and visit the lifeboat station, before a fantastic cliff-top finale to Runswick Bay. 

Highlight: Boulby Cliff rises to 666 feet - the highest point on Britain's east coast. Enjoy cracking views of our walk ahead. 


Option 3 - Saltburn to Runswick Bay

Distance: 11½ miles (18.5km) 

Ascent: 2,100 feet (640m)

In Summary: Enjoy sweeping sea views as we follow the cliff-top path along the coast from Saltburn to Runswick Bay. Our walk takes us over Boulby Cliff to Staithes, then on past Port Mulgrave to Runswick Bay. 

Highlight: Why not celebrate with a cuppa and cake on the beach at the end of the walk in Runswick Bay. 


Head into the heart of the North York Moors, with steam trains on the North York Moors Railway never far away. 

Option 1 - Newtondale

Distance: 6 miles (9.5km) 

Ascent: 550 feet (160m) 

In Summary: Walk over the heather-clad moors from Saltersgate to Levisham in the Newtondale valley, then step back in time with a steam train ride to the market town of Pickering. 

Highlight: Time to explore Pickering - visit Beck Isle Museum, the town's medieval castle, or Pickering Church, home to Britain's most complete set of medieval wall paintings. 


Option 2 - Hole of Horcum

Distance: 9½ miles (15.5km) 

Ascent: 950 feet (280m) 

In Summary: Head into the centre of the North York Moors for this walk which descends into the Hole of Horcum. Our route continues to the village of Levisham, then along the valley into Pickering. 

Highlight: The Hole of Horcum is a huge natural ampitheatre carved into the moors at the end of the last ice age. 



Option 3 - The Bridestones

Distance: 12½ miles (20.5km) 

Ascent: 1,200 feet (380m) 

In Summary: Cross the North York Moors to the ancient Malo Cross and the sandstone outcrop of the Bridestones. We then stride out to Lockton and follow the steam railway to Pickering. 

Highlight: Look out for steam trains. This is Britain's busiest heritage railway, meandering its way through stunning scenery all the way to Whitby. 


Select from a choice of 3 guided walks that head west to walk in the footsteps of Captain James Cook. 

Option 1 - Captain Cook's Monument

Distance: 6½ miles (11km) 

Ascent: 1,000 feet (300m) 

In Summary: Follow the Cleveland Way to the magnificent viewpoint at Captain James Cook’s monument; it's then downhill to the foot of Roseberry Topping and on to the village of Great Ayton. 

Highlight: Walk in the footsteps of Captain James Cook who grew up in Great Ayton. Time to visit the Captain Cook Schoolroom Museum at the end of the walk, or to kick back and relax in the pub. 


Option 2 - Climb the "Matterhorn"!

Distance: 8 miles (13km) 

Ascent: 1,300 feet (400m) 

In Summary: Our route heads up onto the escarpment from near Guisborough, to the summit of Roseberry Topping, then on to the equally impressive viewpoint at Captain Cook's Monument. 

Highlight: The distinctive summit of Roseberry Topping - the Yorkshire Matterhorn. Just tell your mates that you climbed the Matterhorn! 


Option 3 - Cleveland Way leg stretcher

Distance: 10 miles (16km) 

Ascent: 1,700 feet (520m) 

In Summary: A circular walk from Great Ayton, taking in Roseberry Topping and Captain Cook’s Monument. For part of the day our route follows the Cleveland Way along the Moors escarpment. 

Highlight: Soak up the sweeping panorama over the surrounding countryside, and enjoy a walk well worthy of a pint at the end of the day. 


Select from a choice of 3 guided walks that explore the stunning coastline to the south of Whitby. 

Option 1 - Beast Cliff to Robin Hood's Bay

Distance: 6½ miles (10.5km) 

Total ascent: 1,100 feet (340m) 

In Summary: Discover one of the most spectacular sections of the Cleveland Way, to Ravenscar. Following the sweep of the coastline, either along the seashore or along the cliff-top, we'll head for the charming fishing village of Robin Hood’s Bay. 

Highlight: Our walk ends at Robin Hood's Bay where you can explore the narrow cobbled streets, or relax in one of the pubs or teashops. 


Option 2 - Hayburn Wyke to Robin Hood's Bay

Distance: 8½ miles (13½km) 

Ascent: 1,700 feet (520m) 

In Summary: Follow the coastal path from Hayburn Wyke through a nature reserve to Beast Cliff and Ravenscar, then on to Robin Hood’s Bay via seashore or cliff-top paths.                                           

Highlight: The fascinating historic remains of the old Alum works below Ravenscar. 


Option 3 - Cleveland Way to Whitby 

Distance: 18 miles (28.5km) 

Ascent: 3,650 feet (1,120m)  

In Summary: A fantastic leg stretcher for any of you looking for a challenge. The route takes in a superb coastal section of the Cleveland Way, passing through honeypot Robin Hood’s Bay and descending into Whitby following in Dracula’s footsteps.                   

Highlight: the chance to celebrate one heck of a walk - round off the day in Whitby with a well deserved pint of Whitby Whaler, from the brewery across from the Abbey. 


Time to head home. If you've still time or energy to explore further then why not borrow one of our self-guided route cards from our Discovery Point, and enjoy a further walk independently. 

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.

At the house

  • Excellent boot and drying rooms
  • Lounge with a central dance floor
  • One additional lounge
  • 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


All 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


Just 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.

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


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 Good, Better and Best 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 ‘Good’ rooms are ensuite and furnished to a high standard. There are also several ‘Better’ and ‘Best’ Rooms that are either larger or have a desirable view, a more luxurious mattress, larger television, enhanced toiletries and a fluffy bathrobe & slippers – 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. Lunch is a chance to stock up on our famous picnic snacks. Food at Larpool Hall is varied and tasty and has a strong emphasis on ingredients from the area and seasonal produce. Once a week the dining room hosts a Local Food Night, when, over a sociable evening, you might try a five-course feast of local flavours.


For accessibility and assistance information, please contact our expert team on 020 3974 8865

10674_0050 - Larpool Hall - Exterior

Getting to Larpool Hall

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

More Information

What to Bring

“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

6 nights
Outdoor Escapes
Walking Grade:
3 & 4

6 nights from 0pp

...or call 020 3974 8865

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