Cleveland Way - 9 Days & 8 Nights9 Days & 8 Nights 4.7 Read 24 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.
What To Expect
Self Guided | Go at your own pace on an independent active trip.
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
Activity Level & Terrain
This itinerary is graded moderate-strenuous as there are a couple of longer, more challenging days. It 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 be supplied with a detailed map and guidebook so you should have no problem following the route each day.
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, guidebook and map per party.
- 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.
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.
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.
We offer a range of itineraries so you can choose your preferred daily distance so hopefully you will find an itinerary that suits your preferred level of fitness. If you currently don’t enjoy an active lifestyle we suggest regular walking in hilly terrain supplemented by cardio vascular exercise for at least 6 months prior to your walk. A good gym or personal trainer will be able to draw up a personalised training programme.
We suggest you book as soon as you know your plans as the Cleveland Way is extremely popular especially over April/May and July/August.
You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc.
Traditionally April/May has always been the most popular time of year because the theory goes that the weather is better. Although I believe any time between April and October offers a wonderful experience.
We only offer this holiday from Helmsley to Filey in one clockwise direction as the baggage handlers only operate in one way.
Unfortunately we are unable to accommodate walkers with dogs as many of the accommodation providers we use do not accept pets.
You can use public transport or local taxis to continue to your next overnight stop. The Moors Bus operates throughout the North York Moors.
ItineraryDay 1 Arrive Helmsley and overnight
Arrive in Helmsley and check in to your hotel. The rest of the day is yours to explore the nearby sights.
The Feathers is a local landmark standing on the bustling market square in Helmsley. All their rooms are en-suite with colour TV, tea trays, hairdryers and toiletries. The Feathers offers a blend of historic charm and traditional Yorkshire hospitality. You can enjoy informal dining in the Feversham bar or a quiet drink by the fire in the Pickwick bar. Wherever possible they aim to use locally sourced, fresh ingredients.
This charming stone cottage is situated in the middle of picturesque Helmsley, close to the North York moors and nestling by the Hambleton and Howardian Hills.
Red Roofs Bed & Breakfast is set in a lovely country home on the edge of Helmsley, a small market town in the heart of the North Yorkshire Moors.
Arive in Helmsley and take time to wander around the historic village with its picturesque old shops clustered around the market square.
An 18th Century stone inn overlooking the market cross of Osmotherley. The bedrooms are fresh and modern with oak doors and skirting as well as handmade oak wardrobes.
Family owned, with an increasing reputation for high quality, freshly prepared food. The atmosphere at the Three Tuns is always warm, friendly and relaxed and the Rennie Mackintosh inspired interior décor is a delight. The residents lounge is designed to make you feel as though it’s your own home.
This is the most strenuous part of the walk, like a giant rollercoaster walking up and down the Cleveland Hills. The views are stunning across the heather clad moorland and the deep valleys to the south.
The owners extend a warm, friendly welcome at the Buck Inn. Set amidst the rugged splendour of Bilsdale, the Buck Inn offers all the traditions of an English country tavern. The inn provides comfortable accommodation, all guest rooms are situated on the ground floor with private access to the large car park to the rear of the building.
Combining the service and facilities of a Silver Award Winning three-star hotel with the atmosphere of a Yorkshire country inn. The Wainstones provide a friendly and comfortable stay for walkers.
Dromonby Bridge is a Victorian farmhouse situated between Kirkby in Cleveland and Busby, 2 miles south of Stokesley at the foot of the Cleveland Hills. This small B&B is traditionally furnished, rooms are individually designed and have all the amenities you require.
After Clay Bank Top a steep climb leads you to Round Hill and the summit of Urra Moor which is the highest point on the walk. Walking across the moors provides for fantastic walking although watch underfoot as some of the paths can be boggy. The path slowly descends to Kildale passing many burial mounds and boundary stones from the past. From Kildale climb up Easby Moor to Captain Cooks Monument. You are then given the opportunity to climb the eroded sand stone stump of Roseberry Topping before heading downhill to overnight in Newton-under-Roseberry just off the path.
The hotel has been derived from two adjoining quaint 17th Century country cottages that have been extensively re-built and refurbished to create a cosy country hotel.
This family-owned hotel has an enviable reputation spanning over 20 years and is highly-regarded in the region for providing an extensive menu of locally-sourced food.
The walk continues through farmland, woodland and a riverside path leads you to the coastal town of Saltburn-by-Sea where you leave the moors behind and prepare for cliff-top walking along the coastal section.
Welcome to the Victorian guesthouse in the heart of Saltburn and only a five-minute walk from the beach. Features of the rooms include polished floorboards, original water colours, Victorian brass beds, and an open fireplace.
The family-run Spa Hotel is an imposing sight, boasting unrivalled panoramic views of Huntcliff, the North Sea and beautiful surrounding countryside.
You are assured a very warm welcome at the Arches Country House. The Arches is owned and run by the Birkbeck family. The main building was originally a working farm dating back to 1876. Comfortable and relaxing, the bedrooms offer rustic country charm.
From Saltburn the walk now hugs the coastline all the way to Filey. You climb up Hunt Cliff and walk along dramatic sections, passing Rock Cliff (the highest point in the east of England). The path then descends to the pretty village of Staithes with its fleet of Cobles (flat hulled fishing boats from Viking origin). More dramatic coastal paths take you to Whitby with its picturesque harbour and town steeped in history. High above the town are the remains of Whitby Abbey.
Moor Edge is a family run, dog friendly B&B. It contains 2 double guest rooms, each with TVs.
Heathfield Bed and Breakfast guest house in Whitby, North Yorkshire, is a traditional red brick house situated within a short walk of the town centre of Whitby. It is a small family-run guest house with a warm friendly atmosphere.
Boulmer Guesthouse offers a warm welcome in the heart of Whitby. You will enjoy the excellent breakfast using only local produce and fantastic service.
Leaving Whitby pass some small beaches and rock wave cut platforms before arriving picturesque old fishing village Robin Hoods Bay. Perhaps stop to enjoy some lunch in one of the many pubs before continuing to Scarborough.
The entire guest house has been tastefully decorated and lovingly refurbished to the highest standards, with guest comfort in mind. The owners pride themselves on being able to provide all the comforts of home, with a warm and friendly atmosphere - a real home from home!
A lovely Regency Style Grade II listed guesthouse. Offering a warm welcome to walkers and stunning sea views to the south and views of the castle battlements at the front.
Continue down to Filey on the last stage of your walk, looking back at the vibrant colours from South Cliff and reflecting on your walking adventure.
A warm welcome awaits you at The Seafield, 4 Star, Licensed, Silver Awarded Guest Accommodation. You can dine in style on their soft leather, high backed chairs at bespoke solid oak dining tables in their friendly and relaxed dining room.
All Seasons Guest House is a family-run bed and breakfast which has recently been refurbished to a high standard. This boutique guest house combines contemporary elegance and modern convenience with traditional warmth and hospitality. All Seasons is a 5 Star Gold awarded guest house.
Rutland West is a restored Edwardian family run B&B ideally located between the beach and the town center.
Enjoy one last hearty Yorkshire breakfast before checking and making your way to the closest train station or airport for onward travel.
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