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Cleveland Way - 11 Days & 10 Nights

11 Days & 10 Nights 4.7 Read 29 reviews
  • Walking through the untouched landscapes of Northern England.
  • Helmsley Castle and the remains of the Norman Rievaulx Abbey.
  • Clifftop walking along the east coast, with sea views.
  • Crossing open heather moorland skirting the North York Moors.
  • Whitby Abbey, the Captain Cook Monument and Robin Hoods Bay.
The Cleveland Way explores an untouched area of Northern England where dinosaurs once used to roam. On this trail of varying landscapes, from high cliff tops to peaceful moorland, you will continually skirt the North York Moors National Park. Here pilgrims found peace and settled on these moors creating important abbeys and churches, the remains of which can still be seen today. Wander through historic villages, explore picturesque old shops, and enjoy local hospitality. Revel in the impressive views over the Cleveland Hills and also pass Rock Cliff, the highest point in Eastern England. This journey also hugs the coastline and takes you through such charming seaside towns as Saltburn-on-Sea and Filey. Read Ben Lerwill's celebration of the Cleveland Way featured in The Sunday Times.

What To Expect

If you are looking for a spectacular walk with both woodland and coastal walking then the Cleveland Way is for you. It has some challenging sections but it will be well worth it as you will be overwhelmed by the beauty of the area.

Trip Style:

Self Guided | Go at your own pace on an independent holiday.


Inn to Inn Walking | A classic point to point walking trip, staying in a different location each night

This trip is suitable for:

Multi-Generational, Mixed Abilities, First Timers

Ideal if you have an interest in:

  • Historical Journeys
  • National Parks & Trails

Grade & Terrain

This walk is graded moderate and follows footpaths, tracks and cliff paths as well as traversing through fields and moorland. Some of the ascents and descents are steep and can be exposed so require a good head for heights and sure-footedness in places. Please make sure to take extra care when following paths near the cliff edges, especially in wet or windy weather conditions. You should have a good level of walking fitness to get the most from this tour.


Most of the Cleveland Way is waymarked and you will also have access to the macs adventure smartphone app to follow the route each day.

Accommodation Information

One of the highlights of this tour is the friendly and welcoming accommodation. We specifically choose the small hotels, inns, guesthouses and B&Bs to ensure that you enjoy every minute of your stay. All offer a warm welcome to walkers, traditional hospitality and delicious local food.

Solo Walkers & Single Rooms

This holiday is available to solo walkers, although a single supplement is payable. If you require single rooms within your party we would be happy to accommodate your request, although it is not generally possible to secure more than three single rooms in a party. A single supplement is payable.


A hearty breakfast is included each morning. Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will more than happy to provide a packed lunch on request and this can be booked on arrival. Dinner is available either at your accommodation or nearby pubs and restaurants.

  • Accommodation in carefully selected B&Bs, Guest Houses and Country Inns.
  • Breakfast each morning.
  • Door to door baggage transfer.
  • A detailed pre-departure information pack and access to the Macs Adventure Smartphone App
  • Emergency telephone support from our office in the event of a problem.
  • Travel to the start or from the finish of the walk.
  • Lunches, dinners, snacks and drinks.
  • Lunches, dinners, snacks and drinks.
  • Personal Equipment.
  • Extra nights

When To Go

Traditionally April/May has always been the most popular time of year because the theory goes that the weather is better. However anytime between April and October offers a wonderful experience.

Getting to the Start

By Air—The closest airport to the start of the walk is Leeds Bradford International, from here you can catch a train to Malton (55 mins) which is 16 miles from Helmsley, then either a bus or taxi to Helmsley.

By Train—Helmsley doesn't have its own train station and the closest station is 16 miles away at Malton. From the south, trains go via York to Malton, and again you take a taxi or bus to Helmsley. For National Rail timetables, see http://www.thetrainline.com/

By Car—If you plan on driving there is a car park on the north side of town and you can buy weekly parking tickets from the Tourist Information in the market square.

Getting from the End

There are frequent trains from Filey to York, from where there are good connections throughout the UK. If you need to head back to Hemsley then you can catch the train to Malton, and then take a bus/taxi to Helmsley. For the moors and coastal section of the walk there are frequent trains from the south to Saltburn, and you can catch a bus or a train back to Helmsley from Filey.

We are able to book transfers for you as requested - please just get in touch. Full public transport information is detailed in our Information Pack, which we send out with our booking confirmation.

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.  Please ensure that you do not bring more than one bag of 20kg, as if this occurs, the luggage transfer company will ask you to pay an additional fee (approx. £8.50 per day, per bag). This additional payment, should it be necessary, needs to be made locally to the driver and in cash. Any additional bags need to labelled as if they are not labelled we cannot guarantee that they will reach you at the next accommodation.

If you are travelling from far afield and do have more than one bag it is possible to arrange for the extra luggage to be stored whilst you are on the tour for a fee of £25 per bag. These additional bags would be picked up at your accommodation at the start point (Helmsley or Saltburn-By-The-Sea) and dropped off wherever you finish depending on the itinerary you choose to do. Please contact us if you are interested in this option.


You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves, etc.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers for the activity and emergency evacuation and hospital care. 

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Day 1 Arrive Helmsley Day 2 Helmsley to Osmotherley 22 miles / 35.2 km Day 3 Osmotherley to Clay Bank Top 12 miles / 19.2 km Day 4 Clay Bank Top to Roseberry Topping 13.75 miles / 22 km Day 5 Roseberry Topping to Saltburn-by-the-Sea 10.25 miles / 16.4 km Day 6 Saltburn-by-the-Sea to Staithes 9 miles / 14.4 km Day 7 Staithes to Whitby 11 miles / 17.6 km Day 8 Whitby to Robin Hood's Bay 7 miles / 11.2 km Day 9 Robin Hood's Bay to Scarborough 13 miles / 20.8 km Day 10 Scarborough to Filey 10 miles / 16 km Day 11 Onward Travel

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