Cleveland Way

Routes offered on this trail

The Cleveland Way is one of the oldest National trails in Britain.  Starting in the North Yorkshire Market town of Helmsley and finishing in the small seaside village of Filey.  The route will take you over the North Yorkshire Moor's National Park, renowned for the largest expanses of heather moorland in the United Kingdom.  Offering great beauty and tranquillity.    On reaching the seaside town of Saltburn-by-the-sea the path then follows the North Yorkshire coastline south to the small village of Filey.  Passing through quaint seaside villages and the larger vibrant coastal towns of Whitby and Scarborough. The walk offers a wide variety of scenery and terrain.  Only offered in one direction, the route can be walked as a whole or split into two sections. The first half covering the Moors and the second half walking the Coastal route. 

This route can be challenging in a few places, especially on the Cleveland Hills and a some of the Coastal sections. It is classed as a moderate walk. 

On the walk you will have the opportunity to visit Rievaulx Abbey, Scarborough Castle and Whitby Abbey, the inspiration for Bram Stoker's Dracula.            

The mileage shown is from where the Cleveland Way path starts and finishes each day.  A large part of this walk is very rural, so you will find that sometimes the accommodations are very close to the path and other times you will need to walk a little further to your accommodation.  You will not be asked to walk any further than one and a half miles from the path to your accommodation  (The exception to this is at Roseberry Topping, where the only accommodation is 1.5 miles walk, at the bottom of the hill).   If it is further, we will provide you with a taxi to transport you. It really does depend upon the availability of the accommodation and we will not know this until we start booking your rooms.

Cleveland Way.
Full walk 
109 miles / 175 Km

This route is classed as challenging to more challenging

Walk the whole of the 109 miles of the Cleveland Way. Over 8 to 11 nights. From £940.00 per person

Cleveland Way. 
Moors Section. 
57 Miles / 92Km

This route is classed as challenging

Walking the first half of the Cleveland Way, crossing the North Yorkshire Moors.   Covering 57 miles from Helmsley and finishing at Saltburn-by-the-Sea. Over 6 nights.  From £730.00 per person

Cleveland Way. 
Coast Section.   
52 Miles / 84 Km

This route is classed as moderate to challenging

Walking the second half of the Cleveland Way, walking along the Coast.  Covering the 52 miles starting at Saltburn-by-the-Sea and finishing  at Filey. Rated as a moderate to Challenging route, there are areas which are challenging in places. Over 6 nights from £730.00 per person

Rest Days, explore or relax it's your choice. 

A rest day is a great way to break up your walking Holiday.  You could explore the area or just take it easy for the day.  

A fabulous way to make your holiday more bespoke.

We give you some ideas below on choice places to stop for that extra day. 


Taking an additional day at the start of your Cleveland Way walk- you will not regret it.  Helmsley is a picturesque market Town with a 900 year old Castle turned Tudor mansion and a pretty sculptured walled garden.  Some charming tea rooms and a traditional weekly market held every Friday.

Saltburn-by-the -Sea

Whether you are visiting as a finishing point, starting point or as a half way stop Saltburn-by-the-Sea is a great place to take a rest day on the Cleveland way. Offering an excellent place to take in the sights before taking on the coastal section. Full of wonderful places to eat and drink and a good selection of local shops. There is a cliff tramway, the oldest water balanced funicular still operating in Britain. A sand and shingle beach and a Pier.

feet with boots on relaxing in long grass
Two boots tied to a bench


One of the larger coastal Towns on the Cleveland Way.   Whitby Abbey was Bram Stoker's inspiration for 'Dracula'.  In easy walk of the Town.  Captain Cook Memorial Museum, in the house where Cook once lived is well worth a visit if you have chance.   The Church of St Mary looks over Whitby, with 199 steps to reach.  Plenty for you to see and do on your rest day in this lovely coastal Town.

Robin Hood's Bay

Taking an additional day to spend in this picturesque village is a perfect way to Relax.  Amble on the sandy beach or just take time to wander through the narrow, twisting cobbled streets and alleyways.  There is a local museum displaying the history of the old fishing Village.  Also a wide range of places to eat and drink.


What you can expect from this walk

Please see listed below information for this walk.  If you have any questions, please contact us- we will be happy to help.

What is included 

  • You will be accommodated as close to the path as possible in good quality accommodation using a mixture of Guesthouse, Bed and Breakfast, Farmhouse, local Inns and Hotels.
  • All rooms are booked as en-suite or private bathroom wherever possible
  • Breakfast is always included. Sometimes this is continental not always a fully cooked breakfast.
  • Your luggage will be transferred for you between each of your accommodations.
  • Where your accommodation is not within a reasonable walking distance of the path you will be provided with a transfer to your accommodation.
  • Your route planning will be provided as part of your holiday pack.
  • Your Holiday pack will included your Trail Guide and map, itinerary, accommodation directions and route notes, lunch information and evening meal recommendations, luggage transfer information and holiday planning details.
  • A packed lunch and your evening meal are not included in your holiday cost.
  • You will be responsible for getting to your first nights accommodation and departing from your last nights accommodation.  

Additional Costs

Rest Days

If you would like to spend additional days in an area, a rest day can be included in your itinerary.  This is great for exploring the area At £70.00 per person per night.  Please let us know at the time of booking so this can be included.  

Solo Walkers 

Solo walker supplement is charged at £70 per night.  All our walks are based on two people sharing a room.  The Solo Walker supplement is applied per night for anyone holidaying on their own.  It is charged to cover the extra costs passed on from the accommodations and luggage transfers. 

Single Supplement

Single supplement applies if you are booking as part of a group but require a room of your own.  Charged at £60 per person per night. Again, it is charged to cover the extra costs passed on from the accommodations and luggage transfers. 

Postage Costs

Postage is calculated dependant on location, as listed below:

UK - £6.99 per pack

Europe - £17.99 per pack

Rest of World - £26.99 per pack


How to get to the Cleveland Way

Railway stations: Can be found at Saltburn-by-the-sea, Scarborough and Filey..

Car Parking: There is paid parking at Helmsley and on street parking at Saltburn-by-the-Sea and Filey. The only secure parking is at Scarborough

If you would like any help with your arrival or departure arrangements, please contact us at the office where we will be happy to give advice.  call us on +44 (0)7399 330178.


When would you like to start

We want to arrange your holiday to suit you.  So you get to choose the start date and we will work from there.  

Our walks are only offered between April and September, giving better daylight hours and safer walking conditions for you. 


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