In Helmsley:

Helmsley Youth Hostel is a cosy, award winning hostel close to the centre of the town.
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​The Feversham Arms is a luxury hotel with a Spa and swimming pool.
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Stilworth House B and B is situated just off the Market Square and is close to the church. Minimum stay 2 nights. 
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The Feathers Hotel is in the Market Square and is a 16th Century coaching inn.

If you would like to stay in one place for the duration of your walk, you can organise pick-ups and drop offs with Ryedale Executive Drive. Get a quote for the days you need by contacting Helen on 07760160244 or emailing the_teasdales@btinternet.com. Dave and Helen do school runs but are happy to help outside those hours.
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​Along the route:

Shepherd's Hut, Bilsdale is very near the end of Stage 2 - a short walk from St John's Church, Fangdale Beck. Fiona can provide packed lunches and also has farmhouse B and B accommodation.
 
The Buck Inn, Chop Gate is a walkers' inn and already accommodates people walking the Cleveland Way. The owner offers a pick up and drop off service and has agreed to do this from Fangdale Beck at the end of Stage 2. There is also camping available here.
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Bonfield Ghyll Farm has a holiday cottage and pop up campsite and will also pick up and drop off from Fangdale Beck- minimum stay 2 nights.
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High Paradise Farm is slightly off the route but we can provide walking instructions from end Stage 3. There is a variety of accommodation available. Horses can be accommodated in a paddock.

The Owl at Hawnby is a recently refurbished pub close to the end of Stage 3 with comfortable bedrooms and good food.

Easterside Farm B and B is a highly rated farm with accommodation and is just off the walking route at the end of Stage 3 but is close to the riding route. Horses can also be accommodated.

The Lazy T is a luxurious glamping retreat, just off the Trail route near the end of Stage 4. We can provide walking instructions from near the end of Stage 4.

If you would like to do The Trail and enjoy camping contact the following:

Freespirit Glamping is near the beginning and end of the Trail just outside Helmsley and has several glamping tents. It is on a stud farm.

Bonfield Ghyll Farm and The Buck Inn as above- both near end Stage 2

Wethercote Farm Campsite has grass pitches and electric hook-ups plus one bell tent already erected. It is 1.5 miles from the end of Stage 4.

Bungdale Head Camping is near the middle of Stage 7- 01439 770589