Cleveland Way – Journey to the start

I’m sitting in The Feathers pub, an old stone hostelry in Helmsley in the North Yorkshire national park. It’s a Sunday and day trippers are demolishing roast dinners on the surrounding tables. Out of the bay window the light is starting to fade on the ancient market place and a sprightly evening breeze is pushing the clouds along with some pace over the stone and timber buildings that typify Helmsley.

There’s a jovial atmosphere amongst my compatriots and conversation centres around exploits of the day but my mind is elsewhere because I’m precariously balanced on the edge of something good. Tomorrow I’ll check out of my youth hostel and set out on my 10 day walk along the Cleveland Way.

Helmsley Youth Hostel
Helmsley Youth Hostel

Rewind 12 hours. After weeks of planning I have finally packed my rucksack with the items I have been stockpiling for the walk. Weight has been my main headache and the scales say that my load will be 12 kilos, plus water and food for each day.

World on my shoulders
World on my shoulders

Is this good or bad? I don’t know but it feels OK. I’ve been obsessed with minimising weight since my recent trial walk in Devon. I have clothes for half of the walk and will launder them in Saltburn on day 6. I have phoned the laundry – it’s going to work. Yesterday I decided against light shoes for the evenings. I’ll do without. I bought a silk sleeping bag liner from Cambodia so I wont need my sleeping bag at the hostel in Kildale. I’ve left my gaiters and waterproof trousers at home because the long term forecast is dry. Ish.

My planning hasn’t just centred on weight. I’ve packed a single portion of porridge oats for Kildale as there is no shop there. I have plotted all of my destinations on Google maps and pre-cached the map so I should never get lost when out of phone signal range. There are scant few ATMs on the first half of the walk and I’ve taken out cash with which to pay for my first few nights stay. I know which spots are problematic for eating and have plans to stock up at prior locations. I’ve downloaded bus timetables in case blisters prevent me walking any day. And there’s more – much more. So you see, an awful lot of planning has taken place just to get me to the starting line.

And the starting line itself puzzles me. Helmsley is lovely! The 108 mile Cleveland Way starts here and ends in Filey which is, possibly, less lovely. Indeed as it stands I’m planning to walk to the penultimate stop Scarborough and finish the walk there. Who came up with this route?

Short cut
Short cut

The sign to Scarborough is also a little unnerving. It’s 31 miles away and by car you could be sat on the front with fish and chips within the hour. Does walking there over 10 days make any sense

Place of interest
Place of interest

One way of rationalising the walk is that if I don’t do it then I miss out on culinary highlights such as Auntie Anne’s Bakery. I may yet be the first person to complete the walk and actually gain weight. There will also be some fabulous sights en-route and one of the reasons I chose the Cleveland Way is the diversity of scenery.

Lovely Helmsley
Lovely Helmsley

The undeniable attraction of Helmsley will be different to other places I will visit. This pretty, small market town used to play a more significant part in regional affairs as signified by the castle.

Castle
Castle

There’s also a nice church as you might expect, but it’s the softer sights that appeal more to me.

Fun in the allotment
Fun in the allotment

An allotment brings fun and colour to one street. Flowers are in bloom still…

Wild colour

… and especially around the market square…

Helmsley in bloom
Helmsley in bloom

… which draws me back inevitably to food. On this thought and with the aroma of gravy wafting across the panelled dining room of The Feathers it’s time for me to cast aside the planning and rigour of the last few weeks. It’s time to enjoy the fruits of my planning, whatever they may be. I’ll start with a roast and a pint.


It’s the first day of September and almost instantly the temperature has dropped by a few degrees. Today I watched as brown leaves were blown around my feet into piles on the ground for the first time. Signs that our seemingly eternal summer may be on the wane. Tomorrow I may find myself walking into another season.

6 thoughts on “Cleveland Way – Journey to the start

  1. I did the Cleveland Way, in April this year. Lovely walk, although, I backpacked it and did it in 7 days. I’m planning to do it again this October, from Filey to Helmsley “the other way”.

  2. very
    envious – nice to know there are other like minded people in the world! I walk 2 trails (around 70-100) a year on aug. and one at easter with a friend. Can’t wait for easter for next trail.xx Julie x

  3. Thanks for your comments Julie! I’ve met any number of “more serious” walkers on the trail but I’ll just be happy to complete this one. Do you have a trail in mind for Easter?

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