The Cleveland Way was established in 1969 and was the second official National Trail of England (the first being Pennine Way). The trail starts in the beautiful market town of Helmsley and follows a well-trodden trail through the heather-clad moorlands of the North York Moors National Park until you reach the coast. From here, the trail runs down the dramatic North Yorkshire Coastline to Filey, taking in iconic villages such as Robin Hood’s Bay and Whitby (famously the home of Whitby Abbey, inspiration for Bram Stoker’s gothic tale ‘Dracula’).
The scenery experienced along the trail is split into two halves. From Helmsley to Saltburn-by-the-Sea, you will explore the inland geography of North Yorkshire, surrounded by the dramatic moorland landscapes and wild vistas, then spending your evenings in quaint villages tucked away in the valleys. From Saltburn-by-the-Sea to Filey, the scenery shifts, and we begin to experience the rugged Jurassic coastline of North Yorkshire. You’ll walk along the cliffs, looking down to the sea and discovering secluded coves and bays. The atmosphere becomes more vibrant, with vivid seaside towns and perhaps an evening drink watching the sunset.
If you love it so much you’re wanting more, you can extend the route and make it a round trip back to Helmsley via the Tabular Hills Walk (please discuss with us when booking). Alternatively, you could embark on the Yorkshire Wolds Way between Hessle and Filey.
We take the stress out of your trip with expert local knowledge, hand-picked accommodation, luggage transfers and detailed support to help you find your way. You will need full walking kit including waterproof jacket and trousers, a small day sack and comfortable walking boots but you will receive a more detailed kit list upon booking. This trip is based on 2 people sharing, so if you are a solo traveller please contact us for further details and we will be happy to help.
Inclusions
- 9 nights’ accommodation in a good quality B&B or hotel with ensuite or private bathroom and breakfast
- Luggage transfers each walking day
- Map and guide book plus detailed directions to your accommodation from the trail
- Expert local knowledge and 24 hour emergency assistance during your trip
- Professional event organisation
Exclusions
- Travel to the start and finish points of the trip
- Lunches and evening meals
- Personal insurance (for cancellation, accident, health, emergency evacuation and loss, theft of or damage to baggage and personal effects)
- Guiding (please contact us if you would like this trip to be guided)
Optional extras
- Single room supplement £90 per person per night (subject to availability)
- Solo traveller supplement £90 per person per night
- Odd group supplement £90 per group per night may apply if a single room is required
- Extra night prior to start (single room) £180 per person
- Extra night prior to the start (twin room, needs 2 people) £95 per person
- Extra night at the end of the event (single room) £180 per person
- Extra night at the end of the event (twin room, needs 2 people) £95 per person
Please select from Optional Extras at checkout.
Getting there and back
Getting There
By Road: Helmsley can be accessed by car via the A1(M). A19 and A170 – from either the North or the South.
By Public Transport: Train and Bus services are available from York, Northallerton or Newcastle. Check traveline.info for the latest public transport information.
By Air: The nearest airports are Leeds Bradford International Airport or Newcastle International Airport.
Getting Away
By Road: Filey can be accessed by car via the A64 / A170, then across onto the A1(M) to head North or South.
By Public Transport: There are frequent train services running from Filey to Sheffield which take approximately 2.5 hours, or up to Scarborough (15mins) from where you can go back to York.
By Air: The nearest airports are Leeds Bradford International Airport or Newcastle International Airport
Evening meals and lunches
You can purchase evening meals either at the accommodation or nearby. When our event planners send you the schedule with itinerary you could prearrange directly with the accommodation or during the walk.
For lunches we would suggest bringing some of your own favourite snack bars and then asking the accommodation for a packed lunch for the following day and also supplementing that at stops en-route.
Accommodation
Accommodation is generally at B&B, guest houses and small hotels. Once booked in, your event planner will send you a list of your booked accommodation. It is possible to adjust according to preference at this stage so please mention it if you wish to change.
Dog-friendly
If you would like to bring your four legged friend, then we will do our best to source dog friendly accommodation. It is usually possible but if it were not, then we would suggest a change of date to enable it or offer a refund. There may be a small surcharge for the overnight stays. Therefore, once booked in, please alert your event planner that you would like to bring your dog and we can proceed from there.
Need a guide?
If you would prefer to have a guide for your walk, even just for one day, then we are happy to help. We can provide a qualified leader (also first aid qualified) to lead your trek or on just one of the sections. Just ask us.
A guide can not only take the stress out of navigation, but you will also find them a great asset in terms of providing an insight into all things environment and nature.
Dates and prices
For available dates please see the ‘build your trip’ option on the left hand side on desktops or at the bottom on mobiles. You can reserve your space via this route.
After you book
After placing your booking with us, you will in the first instance receive an automated email from our system confirming receipt of your reservation. If you don’t receive it, it is worth checking your spam/clutter folder.
In the process of placing your booking, you will generally set up an access password to our online gateway where you can review the details of the booking.
Your personal event planner will then be in touch with you to start to confirm the details. This contact will usually be taken up in the working day after receipt of your booking, but may, in busy times, take a little longer. The event planner will then liaise with you regarding the details of the course. If you have any specific requirements, please do mention it at this stage.
At the end of your trip
Unfortunately, all good things come to an end at some point and when you arrive at the end of the trail, you have one of several options. If you have not booked an additional night’s stay then we can transfer your luggage to a location of your choice. From there you may have onward travel arranged as per the ‘Getting There and Back’ tab above.
Some people like to treat themselves to a night’s stay at the end. And why not? You’ve earned it. You can arrange this as an optional add on with your event planner.
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