The Cleveland Way in 9 days
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Luggage transfer
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Hotel accommodations
The Cleveland Way will take you through varied and beautiful landscapes. Explore stunning moors, long coastlines, ancient castles and charming fishing villages.
This walking holiday will take you through the North York Moors National Park, where wildlife and cultural heritage blend in to give you a unique experience from Helmsley, where you can visit the National bird of Prey Centre and Helmsley Castle, to Filey.
Finish your tour on the Cleveland Way in Filey, a town with a long golden beach where you can spend the day in the sun.
- Walk the Black Hambelton Plateau, which rises up to 399 metres high.
- Roseberry Topping will be part of this route, a hill known as the Yorkshire Matterhorn.
- Enjoy Whitby's blue flag-winning beaches, representative of sustainable tourism.
- Visit the ruins of Rievaulx Abbey.
Itinerary
Day 1 - Arrival in Helmsley
You can start your journey from Leeds Bradford International Airport or Malton train station. From these two places, you can take a train, taxi or buses that will get you to your destination.
In Helmsley you can visit the National Birds of Prey Centre and Helmsley Castle.
In Helmsley you can visit the National Birds of Prey Centre and Helmsley Castle.
Overnight in Helmsley
The Carlton Lodge
This property is located just outside the North York Moors National Park. Rooms feature Wi-Fi, a flat-screen TV and tea/coffee making facilities.
Day 2 - Helmsley to Osmotherley 22 miles I 35 km
The walk will begin in the direction of the ruins of Rievaulx Abbey, built in order to be the meeting place and for the education of the white monks. One of the best preserved elements is the monks' dining room, almost 38 metres long.
Continue and you will come across Sutton Bank, a hill and nature reserve in the North York Moors National Park in North Yorkshire. Your walk will end in Osmotherley.
Continue and you will come across Sutton Bank, a hill and nature reserve in the North York Moors National Park in North Yorkshire. Your walk will end in Osmotherley.
Overnight in Osmotherley
The Golden Lion
Spend the night in a charming stone house and enjoy a warm stay in your rooms, filled with details such as tiled showers and handmade oak furniture.
Day 3 - Osmotherley to Clay Bank Top 11 miles I 17,7 km
On this day, you will cross the most demanding stretch of the route with extensive ascents and descents across the moors.
The walk will end at Clay Bank Top, located in Bilsdale Valley.
The walk will end at Clay Bank Top, located in Bilsdale Valley.
Overnight in Clay Bank Top
The Buck Inn
It offers 6 ensuite rooms with a flat-screen TV and tea and coffee making facilities.
Day 4 - Clay Bank Top to Newton under Roseberry 13 miles I 22 km
You'll start the this by heading away towards the Urra Moor moor, 454 meters high. In it you will find burial mounds and prehistoric rocks, among which Face Stone stands out.
You will pass through the village of Kildale and Easby Moor Hill. The last leg of the walk will take you to Newton under Roseberry.
You will pass through the village of Kildale and Easby Moor Hill. The last leg of the walk will take you to Newton under Roseberry.
Overnight in Newton under Roseberry
Kings Head Hotel
Stay in a traditional house with spacious and comfortable rooms. You can also enjoy the hotel bar with its pleasant views.
Day 5 - Newton under Roseberry to Saltburn by the Sea 11,5 miles I 18,5 km
You'll start the day by heading away from Newton under Roseberry to Roseberry Topping, a hill known as the "Yorkshire Matterhorn" for its half-cone-shaped summit and jagged cliff. Later, you will pass through the town of Skelton-in-Cleveland, where you can visit the Old All Saints Church.
Cross wooded paths and moors before reaching Saltburn by the Sea, with its Victorian gardens and east-west coast.
Cross wooded paths and moors before reaching Saltburn by the Sea, with its Victorian gardens and east-west coast.
Overnight in Saltburn by the Sea
Victorian Guest House
In this property you will find a restaurant bar and friendly staff who are attentive to every detail.
It offers rooms with Wi-Fi, a flat-screen TV and a private bathroom.
It offers rooms with Wi-Fi, a flat-screen TV and a private bathroom.
Day 6 - Saltburn by the Sea to Whitby 21,2 miles I 34,2 km
Today's walk starts along the coast and then has an ascent to the highest point of eastern England, Rock Cliff. Later, the road descends to the pretty village of Staithes, situated in a small bay.
You will return to the coast to finally reach Whitby, known for its blue flag-winning beaches, representative of sustainable tourism; and for its steam train, the North Yorkshire Moors Railway.
You will return to the coast to finally reach Whitby, known for its blue flag-winning beaches, representative of sustainable tourism; and for its steam train, the North Yorkshire Moors Railway.
Overnight in Whitby
Mooredge B&B
This property is a 15-minute walk from the town centre and 800 metres from Whitby Museum.
It features Wi-Fi, a lounge and rooms with views of the Esk Valley.
It features Wi-Fi, a lounge and rooms with views of the Esk Valley.
Day 7 - Whitby to Scarborough 22,3 miles I 36 km
Head to Robin Hood's Bay, a fishing village on the coast of the North York Moors, where you can take a break and find a variety of pubs, cafes and restaurants.
The walk continues to Scarborough, one of the most popular holiday destinations in the UK. Here you can visit the Geology Museum and Scarborough Castle.
The walk continues to Scarborough, one of the most popular holiday destinations in the UK. Here you can visit the Geology Museum and Scarborough Castle.
Overnight in Scarborough
Toulson Court
Located on Scarborough's north coast, this guest house is just a 10-minute walk from the town centre and the promenade.
Its modern rooms feature a private bathroom, a flat-screen TV, Wi-Fi and a drinks tray.
Its modern rooms feature a private bathroom, a flat-screen TV, Wi-Fi and a drinks tray.
Day 8 - Scarborough to Filey 9,3 miles I 15,1 km
Finish your tour of the Cleveland Way in Filey, a town with a large golden beach where you can spend the day in the sun. Porpoise sightings are common in summer and during spring you're likely to encounter a seal sleeping on the beach.
Overnight in Filey
The Seafield Guest House
This guest house is attended by its owners, who will give you a warm welcome and take care of detail, so that you have a comfortable stay.
Rooms feature Wi-Fi, a flat-screen TV and tea/coffee making facilities.
Rooms feature Wi-Fi, a flat-screen TV and tea/coffee making facilities.
Day 9 - Filey
After enjoying your breakfast, you can head to Filey train station, where there are several routes to the whole of the UK.
To return to Hemsley, first take the train to Malton and then a bus or taxi.
End of our services.
To return to Hemsley, first take the train to Malton and then a bus or taxi.
End of our services.
Itinerary map
Services
Included
- Accommodation in en suite rooms in charming hotels
- Daily Breakfasts
- Luggage transfers between accommodations
- Information dossier with maps and routes
- 24-hour telephone support
- Sustainable travel, we compensate the CO2 emissions of your trip
- Taxes
Extras
- Travel insurance
- Cancellation insurance
- Additional nights
Accomodation
General information
The accommodations with which we collaborate have a private bathroom and all the necessary services to ensure the best comfort available.
Our team checks in situ the quality of all the accommodations offered, so that you have an unforgettable experience during your trip.
The accommodation that we will book for your trip will be selected taking into account our commitment to you: guaranteeing comfort, calm and enjoyment throughout your trip.
We work with quality hotels and country cottages with limited capacity, so we invite you to confirm your reservation as soon as possible.
The name of each accommodation will be provided to you a few weeks before your trip begins.
Room types
It is possible to book this journey in single, double or triple rooms.
All rooms have private bathrooms.
Travel & transfers
We recommend starting your trip at Leeds Bradford International Airport, where you can take a train to Malton, then you can head to Helmsley by bus or taxi.
If you're travelling by train, head to Malton station and take a taxi or bus to get to your destination.
At the end of your route, you will be able to head to Filey train station, where there are several routes to all parts of the UK.
To return to Hemsley, first take the train to Malton and then a bus or taxi.
If you're travelling by train, head to Malton station and take a taxi or bus to get to your destination.
At the end of your route, you will be able to head to Filey train station, where there are several routes to all parts of the UK.
To return to Hemsley, first take the train to Malton and then a bus or taxi.
FAQs
Is luggage transfer included? What are the luggage requirements?
Absolutely! Each traveller has included 1 piece of luggage that we will transfer between your accommodations. It's important that this piece of luggage meets the following criterias:
- Maximum weight of 40 lbs (18 kg).
- Must be only 1 piece of luggage without any attachments or accessories.
- Should not contain valuables, fragile items, food or medications.
- Must be correctly identified (booking reference of your trip and the full name of the trip holder).
How far in advance should I book my trip?
We recommend that you book as soon as you are sure about your dates, as accommodation can fill up very quickly in this area.
What is the best time of year to do this trip?
This walking holiday is available between spring and autumn, from April to October.
Traditionally, the busiest months for tourists are April and May when considering the weather to be more favourable.
What should my physical preparation be?
This route has a low to average level of difficulty, with quiet journeys and some stretches of walking through steep sections, steep roads and heights reaching 1,490 feet above sea level.
To make the most of this route we recommend you exercise regularly for a couple of months before starting it.
What equipment do I need to bring?
Once you make your reservation we will send you all the detailed information about the specific equipment you need for this route, considering recommendations for shoes, boots, clothes and a day-to day backpack.
What if I'm not able to finish one of the stages?
You can call us to arrange a private transfer for you.
If you prefer, you can also use public transport or local taxis to get to your next accommodation.
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