Cleveland Way - 10 Days & 9 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.
ItineraryDay 1 Arrive Helmsley
Arrive 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.
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, with a few climbs as you follow the old Drovers road to Black Hambelton. The day ends in Osmotherley; a quaint village with old pubs, shops and cafes.
Ascent: 545m / Descent: 440m
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. After a fairly easy start, prepare for switchbacks and a succession of ascents and descents toward Clay Bank. The views are stunning across the heather-clad moorland and the deep valleys to the south.
Arriving at the Clay Bank Top junction you will get a transfer to your accommodation in the surrounding area.
Ascent: 700m / Descent: 600m
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 Buck Inn is located in South Chop Gate. 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.
A transfer will take you back to Clay Bank Top, where a steep climb awaits, leading 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 allowed to climb the eroded sandstone stump of Roseberry Topping before heading downhill to overnight in Newton-under-Roseberry just off the path.
Ascent: 540m / Descent: 700m
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 that 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.
Ascent: 450m / Descent: 545m
The family-run Spa Hotel is an imposing sight, boasting unrivalled panoramic views of Huntcliff, the North Sea and beautiful surrounding countryside.
Ensure you book a table at their recently refurbished restaurant. We recommend timing it with the sunset!
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 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.
Ascent: 595m / Descent: 600m
The Corra Lynn B&B is a family-run B&B, located on the West Cliffs of Whitby. Each room comprises TV with free view, tea and coffee facilities, mini fridge, luxury soft towels and free WiFi.
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.
Apart from a few steep inclines, the walk to Robin Hood's Bay is gentler and allows you to turn your attention to the grassy cliff paths that are cut above smuggler's coves with wide-reaching views. Follow onward past some small beaches and rock platforms shaped by the sea as you head into the iconic town of Robin Hood's Bay.
Robin Hood's Bay is where Wainwright's C2C national trail ends, so there will be plenty of fellow walkers in the local pubs where you can chat about the day's endeavours!
Ascent: 190m / Descent: 205m
The Villa was built in 1892 as a lodging house, the first of its kind, at the top of Bay Bank. This Victorian property has been lovingly restored retaining all its original features; servant bells, original cast iron fireplaces in all bedrooms and a cast iron range in the kitchen.
A large detached Victorian House in Robin Hood's Bay, built-in 1897 by Captain Jacob Storm. Lovingly restored with many original features and located a short stroll away from the beautiful cobbled streets which wind down to the sea, passing a variety of local restaurants, pubs and shops.
The Victoria Hotel is a landmark hotel on the cliff top at Robin Hood's Bay. The building is a superb example of a Victorian Hotel built around 1897 with a fantastic open, wooden staircase. The hotel boasts spacious rooms, free wifi, sea view restaurant, and sea view tea room.
Ascent: 275m / Descent: 310m
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!
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.
Your destination today is Filey Brigg, the end of the Cleveland Way. Head out from Scarborough along more cliffside grassy tracks with a few ascents and descents. Be sure to savour this final stretch, looking back at the vibrant colours from South Cliff and reflecting on your completing the wonderful walking adventure!
Ascent: 165m / Descent: 165m
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.
Other InformationIs 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.
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.
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.
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 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
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. 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.
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