Cleveland Way - 9 Days & 8 Nights
- 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.
Gallery
Itinerary
Day 1 Arrive Helmsley and overnightArive in Helmsley and take time to wander around the historic village with its picturesque old shops clustered around the market square.
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.
The site of The Black Swan dates back to the 15th century, the house itself comprising of a Tudor house, a Georgian house, and an Elizabethan house.
This accommodation offers a warm welcome with cosy rooms, an in-house bar and restaurant, and easy access to Rievaulx Abbey, Helmsley Castle and Helmsley Walled Garden.
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.
The first highlight of today's walk, Rievaulx Abbey ruins are worth the half a mile detour off the path, set in the wooded valley of the river Rye. As you approach Sutton Bank the Kilburn White Horse - a limestone horse created by removing down turf can be seen. The views from Sutton bank are wonderful and the walking easy with a few climbs as you follow the old drovers road to Black Hambelton. The Days walking ends in Osmotherley; a quaint village with old pubs, shops and cafes.Â
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.
The Queen Catherine Hotel is a family-owned pub offering food and accommodation in the heart of the North Yorkshire Moors. The hotel has a small selection of comfortable and well-appointed bedrooms, all of which have just been highly refurbished.
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.
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.
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.
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.
The family-run Spa Hotel is an imposing sight, boasting unrivalled panoramic views of Huntcliff, the North Sea and beautiful surrounding countryside.
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.
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.
The Corra Lynn B&B is a family-run B&B, just a two-minute walk from Pannett Park and five minutes to Whitby Town Centre and 5 mins to the beach.
The Duke of York is a charming inn that offers a comfortable Bed & Breakfast, and is located in the hart of Whitby at the bottom of the 199 steps. The B&B offers a warm and welcoming pub, which offers traditoonal pub food. There are 8 en-suite rooms in the Inn, that are dog friendlt. All of the rooms offer en-suites with showers, towels, bathmats, shower gel and handwash, and the rooms offer tea and coffee making facilities, a TV, hairdryer and suitcase rack.
Number 4 Bagdale is only a few steps away from Bagdale Hall. This Georgian townhouse, with a grand and imposing façade, was probably built for a wealthy businessman or ship-owner. In times past this building has been called ‘The Bagdale’, a hotel in its own right, many years ago. The interior matches the formal grace and understated grandeur of the outside and features rooms with high ceilings and a Palladian stained glass window at the rear of the house.
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 property has been beautifully restored and retains many original features. All 7 rooms are individually designed, decorated to a high standard and benefit from ensuites. With all the modern comforts you would expect to make your stay special such as top of range beds, luxury Egyptian cotton linen, thick fluffy towels, free high-speed WiFi, flatscreen UHD Smart TVs (with Netflix and other on-demand services) and stocked with Noble Isle toiletries.
There is no such thing as a standard room at The Waves. Each of their 7 rooms are unique – individually decorated and furnished to reflect the elegance of the late victorian building, with the added benefit of state-of-the-art Smart TVs and luxury beds.
A bright, modern hotel in the heart of Scarborough with all the facilities walkers could wish for including a boot washing station and drying area! Add to that comfortable and spacious rooms and a warm welcome and you'll be sure of a lovely stay in Scarborough!
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.
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.
This trip has a carbon score of 8kg per person per night, meaning it’s one of our greenest trips! For comparison, a carbon count of 8kg is equivalent to 12 pints of local beer at a bar. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information about how we've carbon counted our trips.
Other Information
Is it for me?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.
Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way, Tour Du Mont Blanc and the Passau to Vienna Danube Cycle Path, to name but a few!
Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.
Solo Travellers
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.
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.
Meals
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.
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.
- 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
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.
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.
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.Â
At Macs Adventure, we work in partnership with many luggage transfer providers who set a limit on how many bags/suitcases they will transfer per person, and also the weight of the bag/suitcase. Your booking includes transfer of 1 bag per person. It is very important that you read the luggage information specific to your tour before departure. If you do not adhere to these limits, there is a great possibility that you will be charged locally both for extra bags or if they are too heavy. This limitation can be a challenge, especially as airlines generally have limits that are higher. However, our luggage providers have reasons for these limits (usually due to the Health and Safety of their employees), which we must respect.
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.Â
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.
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.Â
You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc.Â
You can use public transport or local taxis to continue to your next overnight stop. The Moors Bus operates throughout the North York Moors.
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