The Cleveland Way
12 Days Starting in Helmsley, England and ending in Filey, England
Visiting: Helmsley, Sutton Bank, Osmotherley, Great Ayton, Saltburn-by-the-Sea, Whitby, Scarborough, Filey
Tour operator:
Tour code:
WCX
Group Type:
Independent
Guide Type:
Self Guided
Tour operated in:
EnglishTrip Styles:
Interests:
Activities:
Tour Overview
Embark on an unforgettable journey along The Cleveland Way, a captivating walking tour through the stunning landscapes of North Yorkshire, England. This self-guided adventure offers a perfect blend of coastal and moorland walks, rich with historical interest and breathtaking views. Over 11 nights, you'll stay in charming guesthouses and hotels, enjoying daily breakfasts and the convenience of luggage transfers. Highlights include the ruins of Rievaulx Abbey, the dramatic cliffs of Rock Cliff, and the picturesque fishing village of Staithes. With manageable daily distances and a mix of terrains, this tour provides a rewarding challenge without being overly strenuous.
Highlights
Itinerary
Day 1 : Arrive Helmsley
Location: Helmsley
Accommodation Name: The Black Swan
Make your own way to Helmsley and settle into this attractive old market town. Visit the ruins of the castle keep with echoes of the English Civil War in 1644. There are a couple of nice pubs to visit.
Accommodation: The Black Swan is a wonderful pub dating back to the 15th century. With an Elizabethan building on one end, a Tudor one to the other and a Georgian House in the middle, the Black Swan is wonderfully higgledly-piggledy, with bags of character.
Day 2 : Helmsley To Sutton Bank, Return To Helmsley To Overnight 15.4 Km/9.6 Miles
Location: Helmsley
Meals Included: Breakfast
After breakfast depart Helmsley on this easy section across the wooded Rye Valley, then ascend gently up to the Tabular Hills and onto the great viewpoint at Sutton Bank, with views to a Victorian chalk horse carved into the hillside. Enroute you can visit the famous 12th century Rievaulx Abbey. A transfer has been arranged to pick you up from Sutton Bank and you will return to Helmsley for the night (included in cost).
Day 3 : Transfer To Sutton Bank Then Walk To Osmotherley 18.5 Km/11.5 Miles
Location: Sutton Bank
Accommodation Name: Vane House
Meals Included: Breakfast
After breakfast, you will be transferred back at Sutton Bank. Today is more or less level walking along the escarpment of the Hambleton Hills with views over the vale of York. The walk follows the ancient Hambleton Cattle Drovers Road to the old market and mining village of Osmotherley with the remodeled 15th century church with 12th century Scandinavian carvings.
Accommodation: Vane House is a large old stone guesthouse. A friendly welcome is offered and all spacious rooms are ensuite.
Day 4 : Osmotherley To Clay Bank Car Park 20.9 Km/13 Miles
Location: Osmotherley
Accommodation Name: Wainstones Hotel
Meals Included: Breakfast
After the warm up of the last couple of days, hopefully you are ready to enjoy what most people would claim to be the hardest day of the route, as you are ascending and descending over a succession of moors to Clay Bank Top. The views in reasonable weather are extensive. The Coast-to-Coast shares this day and it is a roller coaster ride of a walk up and down beside the crags of Cringle Moor and the famous Wainstones.
We come off the ridge at Clay Bank Top and you will get a transfer to your accommodation (included) from the car park at Clay Bank Top to Great Broughton.
Accommodation: Great Broughton - Wainstones Hotel, this present day structure has developed around a former dwelling dating from early 1700.
Day 5 : Clay Bank Top Car Park To Great Ayton 14.8 Km/9.2 Milies
Location: Great Ayton
Accommodation Name: Royal Oak Hotel
Meals Included: Breakfast
Transfer back to Clay Bank car park and then you start the day with a steep ascent up onto Urra Moor and the highest point of the journey at Round Hill 454m. You are now walking on exposed high moorland, following the line of the disused Ironstone railway line and drovers roads, with many ancient features, such as boundary stones, tumuli and cock pits before descending to cross the remote hamlet and railway station at Kildale. Ascend again, passing the Captain Cook memorial.
Accommodation: Royal Oak Hotel this 18th century rural hostelry is at the heart of the village. Original features include the beamed ceilings and welcoming log fires, which add to the charm and character of this traditional inn.
Day 6 : Great Ayton To Saltburn 23.6 Km/14.7 Miles
Location: Saltburn-by-the-Sea
Accommodation Name: The Victoria Guesthouse
Meals Included: Breakfast
The walk continues through forests with a diversion to “Rosberry Topping” an outlying craggy hill. It is a steep climb, but the views on a clear day are outstanding. The trail follows more moorlands and then through the Guisborough woods and steeply down to Slapewath, an area of old mineral workings. Perhaps fortify yourself with a pint before continuing the last 7 km/ 4.5 miles to Saltburn-by-the-Sea; an old fishing village; come small Victorian seaside resort that was once famed for salt making and smuggling! The whole nature of the walk changes from here as you head off along the coast.
Accommodation: The Victoria Guesthouse is a family run guesthouse is situated only a few hundred yards from the beach.
Day 7 : Saltburn To Runswick Bay 19 Km/12 Miles. Bus To Whitby
Location: Whitby
Accommodation Name: Chiltern Guesthouse
Meals Included: Breakfast
Walk along successive dramatic cliffs, past the highest point on the English east coast at “Rock Cliff” near Boulby. Highlight of the walk today is the beautiful little fishing village of Staithes. The fishing boats at the quay are called Cobles and they still set out to undertake this dangerous activity. Captain Cook served his apprenticeship in a shop on the seafront which has long ago, been stolen by the sea! The trail continues onto the red roofed attractive village of Runswick Bay, by the Jurassic shale cliffs, a fossil hunter’s paradise! It is difficult to secure 1 night stays in Runswick Bay so we will book a 2 night stay in Whitby. You can easily move between Runswick Bay & Whitby on the bus (own expense) or alternatively we would be happy to organise a return taxi transfer for you (own expense).
Accommodation: Chiltern Guesthouse is a small seaside BB situated close to the harbour and beach. Of course this is a busy town and alternative accommodation will be used.
Day 8 : Bus To Runswick Bay And Walk To Whitby Bay 13.5 Km/8.5 Miles
Location: Whitby
Meals Included: Breakfast
Start your day with a short bus ride back to Runswick Bay (own expense).
Quite a short day giving you the chance to have a good look round Whitby Bay. From Runswick, there is another section of cliffs before reaching Sandsend, from where you walk along above the beach to Whitby Bay. This red roofed town grew rich especially between 1750 and 1850 on fishing, whaling, jet mining and shipbuilding. Whitby is also famous for its Abbey ruins and for Count Dracula (there is a Dracula Trail in the town). We would recommend that of all the places on this route, you have a fish meal here!
Day 9 : Whitby Bay To Robin Hood’S Bay 10.5 Km/6.5 Miles
Location: Whitby
Accommodation Name: The Villa Guesthouse
Meals Included: Breakfast
The shortest day, giving you the opportunity for a leisurely breakfast and late start. The climb out of Whitby Bay involves 199 steps and takes you up to the old abbey ruins, and to St Mary’s church with its boat deck construction inside. The trail then follows the coastal cliffs once more, with good bird life, depending on the time of year! You then rejoin the Coast-to-Coast trail for the last few miles into Robin Hood Bay. This little places drops steeply down to the sea and the Bay Hotel is a good place to sit with a beer on the ocean terrace, watching the sea and all those people celebrating that have just completed the Coast to Coast walk.
Accommodation: The Villa Guesthouse is is elegantly refurbished Victorian guesthouse with many original features.
Day 10 : Robin Hood Bay To Scarborough 24 Km/15 Miles
Location: Scarborough
Meals Included: Breakfast
After a couple of easy days, you now have quite a long one to the seaside resort of Scarborough, certainly the largest settlement that you will visit on this tour! The route goes past the planned for but abandoned resort of Ravenscar where the Victorian street layouts can be detected where the grass has receded. At nearly 200 metres high, you will get possibly the most beautiful view of the Yorkshire coast. You then follow the cliffs gradually descending into Scarborough with its two sandy bays, castle remains on a headland and chances for swimming, ice cream etc. This is said to be the first English seaside resort, having long been associated with spring waters from the 1600s.
Accommodation: We use a number of guesthouses in this busy seaside town.
Day 11 : Scarborough To Filey 17 Km/10 Miles
Location: Filey
Accommodation Name: Rutlands West Guesthouse
Meals Included: Breakfast
The last stretch of your walks meanders along behind Cayton Sands and then along the cliffs again to the calcareous grit stone promontory at Filey Brigg (also a nature reserve). If it is low tide, you can cross the sands to finish at Filey, otherwise you need to retrace your steps to get round to this pleasant fishing
esort town.
Accommodation: Rutlands West Guesthouse is a beautifully refurbished Edwardian B&B, it is well situated between the town & beach.
Day 12 : Arrangements End After Breakfast
Location: Filey
Meals Included: Breakfast
Depart Filey after breakfast.
What's Included
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Accommodation
11 nights in guesthouses and hotels -
11 breakfasts
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11 nights accommodation in guesthouses and hotels on a twin share basis with ensuite facilities where available
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One piece of luggage per person transferred from Inn to Inn, not exceeding 18kg
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Digital information pack including route notes & maps
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Emergency hotline
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Return transfer Helmsley/Sutton Bank
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Return transfer Clay Bank Top/Great Broughton
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GPX Files
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Lunch, Dinner and drinks
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Entrance fees
What's Not Included
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Lunch, Dinner and drinks
Lunch, dinner, and drinks are not included.
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Entrance fees
Entrance fees to attractions are not included.
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Travel insurance
Travel insurance is not included.
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Travel to the start and from the end point of the trip
Travel to the start and from the end point of the trip is not included.
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Personal expenses such as laundry and phone calls
Personal expenses such as laundry and phone calls are not included.
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Unscheduled transfers required during the trip
Unscheduled transfers required during the trip are not included.
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Cost of bus between Runswick Bay & Whitby return
The cost of the bus between Runswick Bay and Whitby return is not included.
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A supplement will apply if you are travelling solo or book a single room
A supplement will apply if you are travelling solo or book a single room.
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Guide - this is a self guided holiday
A guide is not included as this is a self-guided holiday.
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Excess Luggage
Excess luggage is not included.
Accommodation
11 nights in guesthouses and hotels. Described is the normal accommodation that we use on this tour. At the time of booking please be aware that other places might be used instead, if these choices are full or closed for whatever reason. Rooms generally do not have baths. The main reason being that they take up a lot of space, some hotels/guesthouses may have a separate room in the house where a bath is available to guests, but in the main it is showers.
What You Carry
As the walks are fully supported you only need to carry a daypack with your daily requirements including raincoat, lunch supplies, waterbottle, warm top, camera etc.
Grading
Not particularly long days but some steep climbs and descents. Generally, however undulating. Mixed weather can be expected. We would not recommend the route for first time walkers.
Mode of Transport
Return transfers are provided from Helmsley/Sutton Bank and Clay Bank Top/Great Broughton. Additionally, there is a bus between Runswick Bay and Whitby, and a cost of bus between Runswick Bay & Whitby return.
Check out our Q&As
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What type of accommodation is provided during the tour?
The tour includes 11 nights in guesthouses and hotels. Rooms generally do not have baths, but showers are available. Some hotels or guesthouses may have a separate room with a bath available to guests.
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Is luggage transfer included in the tour?
Yes, one piece of luggage per person, not exceeding 18kg, will be transferred from Inn to Inn.
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What meals are included in the tour?
The tour includes 11 breakfasts. Lunch, dinner, and drinks are not included.
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Is there any emergency support available during the tour?
Yes, an emergency hotline is available during the tour.
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Are there any transfers included in the tour?
Yes, return transfers from Helmsley to Sutton Bank and from Clay Bank Top to Great Broughton are included.
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What should I carry during the walks?
As the walks are fully supported, you only need to carry a daypack with your daily requirements including a raincoat, lunch supplies, water bottle, warm top, and camera.
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Is this tour suitable for first-time walkers?
The tour is not recommended for first-time walkers due to some steep climbs and descents, as well as mixed weather conditions.
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What happens if the usual accommodation is not available?
If the usual accommodation is full or closed, other places might be used instead.
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Is this a guided tour?
No, this is a self-guided holiday. An information pack including route notes and maps will be provided.
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Are there any additional costs I should be aware of?
Yes, additional costs include travel insurance, travel to the start and from the end point of the trip, personal expenses such as laundry and phone calls, unscheduled transfers required during the trip, the cost of the bus between Runswick Bay and Whitby, and a supplement if you are traveling solo or book a single room.
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Self-guided holidays - inclusions
We have designed our self guided walking and cycling tours to include a number of elements to help you enjoy your holiday more, while leaving out some things to give you more freedom to tailor the trip to your needs and interests. Refer to the Trip Notes for more information on the specific inclusions for each trip. What’s included: - Detailed Route Notes - Accommodation - Luggage transfers - Any scheduled transfers as per Trip Notes - Emergency support - Some meals (mostly breakfasts) What’s NOT included: - Transport to/from start/finish points - Most meals - Any entrance/park fees - Travel insurance - Personal expenses along the way - Unscheduled transfers required during the trip
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Trip Grading & Preparation
Match your level of fitness & requirements Please read this information carefully to find out which grade is most suited to your level of fitness and requirements. To make the most of your Walkers' Britain holiday it is essential and your responsibility to choose a trip that is well within your capabilities. All our active holidays are graded and clearly marked in each trip description. All mountains have uphill and downhill sections and by definition walking and cycling demand some effort. However all things are relative, and these grades assume that you are a reasonably active person who enjoys walking or cycling. Few trips are extreme and most allow ample time for sightseeing and enjoying the scenery. If in doubt about the grade of any holiday, please contact us for advice or request the tour dossiers, you can also chat with our team about the right travel insurance for you. Grade 1 – Introductory These trips involve walking for four to five hours per day or cycling for 15-50 km per day at a slow but steady pace. You will need a reasonable level of fitness and good health. Suggested Preparation 30 minutes of aerobic-type exercise (either road cycling or jogging), three times a week for three months leading up to your trip. Grade 2 – Introductory to Moderate These trips involve a combination of what is described in our Introductory and Moderate levels. The emphasis is on introductory activity but including several moderate stages. Grade 3 – Moderate These adventures involve walking for up to six hours per day or cycling for up to 65 km per day, at a steady pace. You will need a good level of fitness and be in good health. Suggested Preparation 45 minutes of aerobic-type exercise (road cycling or jogging) three times a week for three months leading up to your trip. Grade 4 – Moderate to Challenging This trip grading involves a combination of what is described in our Moderate and Challenging levels. The emphasis is on moderate activity but including several challenging stages. Grade 5 – Challenging These active holidays involve walking up to nine hours per day in mountainous terrain with steep ascents and descents, pass crossing & alpine weather conditions, or cycling for up to 80 km per day over undulating terrain, with some steep and sustained hills. You will need an excellent level of fitness, be prepared to carry a daypack weighing up to 8 kg and be completely comfortable in adverse weather conditions. Suggested Preparation 1 hour of aerobic-type exercise five times a week for three to six months leading up to your trip. We also recommend regular hill walking with a pack in variable weather conditions or road cycling.
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Route notes
While our tours vary in terms of difficulty, route finding is made simple and convenient with our specially prepared package of maps and route notes. On many of the walks it is easy enough to navigate carefully using the route notes provided with a cursory glance at the map. As holidays reach the higher grades, you will need to take more care and we would expect you to have at least some knowledge of using a compass. Maps for our tours also vary considerably, from up-to-date GPS referenced additions, to old map copies which may still be the only ones obtainable for a particular area. The differences in style, grade and destinations of our tours are features that make them of continual interest and delight to our walkers & cyclists. Each set of route notes can contain the following elements relevant to the route: History and information on the region and the route you are walking. Detailed maps including points of interest and accommodation. Detailed step-by-step descriptions (with pictures) of the route and information on detours/optional additions. Transport timetables and information for getting there and away. Safety information and advice. Contact details of accommodation, transport, local representatives and emergency support. Advice for things to do along the way. Suggestions for dining and self catering.
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How our self-guided holidays work
Self guided walking and cycling holidays offer freedom, independence and choice, allowing you to tailor your holidays in the UK & Europe to your interest and travel style. Our detailed Route Notes will contain all of the information you need to plan how you would like to approach each day, giving you the freedom to set your own pace. As you are not limited by the constraints of group travel, you are free to shorten or lengthen your walk as the terrain permits and can even take a day off, although you may need to travel onto your next accommodation by taxi or public transport in order to do so.
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Oct 05, 2025 - Oct 16, 2025Book with Confidence
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Low Deposit
Walkers' Britain requires a minimum deposit of 250 GBP per person or the full booking value, whichever is less, with the final balance not due until 70 days before departure.
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Cancellation Policy
We don't charge a cancellation fee, here is a summary of walkers' britain charges.
Up to 70 days before tour starts: Forfeit 100% of deposit.
At 69 days before tour starts: Forfeit 50% of booking price.
At 35 days before tour starts: Forfeit 100% of booking price.