“Sometimes it snows in April.”

(Prince Rogers Nelson, 7 June 1958 – 21 April 2016)

  • DATE OF WALK: Thursday 21st – Friday 29th April 2016 (9 days)
  • START: Helmsley, North Yorkshire (marker post)
  • END: Filey, North Yorkshire (marker/Filey Brigg)
  • LENGTH: 110 miles


  1. Helmsley to Sutton Bank (10 miles, plus 1 mile to accommodation in Kilburn) – 21 April
  2. Sutton Bank to Osmotherley (12 miles) – 22 April
  3. Osmotherley to Clay Bank Top, nr Great Broughton (11 miles) – 23 April
  4. Clay Bank Top to Slapewath (20 miles, plus detour to climb Roseberry Topping) – 24 April
  5. Slapewath to Skinningrove (8 miles) – 25 April
  6. Skinningrove to Sandsend (13 miles) – 26 April
  7. Sandsend to Robin Hood’s Bay (10 miles) – 27 April
  8. Robin Hood’s Bay to Scarborough – Spa (16 miles) – 28 April
  9. Scarborough – Spa to Filey (10 miles) – 29 April

For a clickable map and lots of other helpful information, see the National Trail website here.


Eve – Royal Oak, Helmsley

  1. Forresters Arms, Kilburn
  2. YHA, Osmotherley (aka Cote Ghyll Youth Hostel)
  3. Wainstones Hotel, Great Broughton (NB: By prior arrangement you can call hotel from the actual Wainstones when approx. ½ hour from Clay Bank Top. Wait in huge layby/picnic spot. Driver will take you approx. 2½ miles to hotel. Arrange drop-off for following morning.)
  4. Fox and Hound, Slapewath, nr Guisborough
  5. Parents’ cottage, Skinningrove (possibly available for public booking in future, but not yet!)
  6. Discovery Apartment Bligh, Whitby
  7. Grosvenor Hotel, Robin Hood’s Bay
  8. YHA, Scarborough
  9. Returned home by train from Filey


My Cleveland Way story really begins on Monday 21st December 2015. That evening, my beloved grandmother (83), suffered a fall at her home which badly hurt her shoulder and upper arm and left her breathless. She was in hospital over Christmas and for the first few weeks of January. During this period the family received mixed messages from staff about her prospects for coming home, but nothing definitive. Meanwhile she was also having chest X-rays…

…and on 24th January her children (my mother and her sister) were told that, in fact, she had lung cancer and the consequences of the fall were not the most pressing issue. A bronchoscopy confirmed that it was small cell lung cancer, which meant she had weeks to live. She decided against chemotherapy and came home on 10th February. It was a blessing that she remained lucid and happy until just a few days before her death, on 20th March. I wrote (but could not read out) the eulogy at her funeral on 6th April.

In the meantime, a sort of collective grief had begun to characterise the year 2016, at least for those people fully engaged with the popular culture of the latter half of the 20th century. Most such people date the onset of this feeling to the announcement, on the morning of 11th January, that David Bowie had died, two days after his 69th birthday and the simultaneous release of his album ‘Blackstar’. I and hundreds of thousands of others will always remember this being announced by Shaun Keaveny on the 6Music breakfast show, after an eerie 10 minutes or so with three consecutive records, no 7am handover and no chat. What followed was, incidentally, a feat of spontaneous and heartfelt public service broadcasting that deserves never to be forgotten, for which Mr Keaveny and his team have been thanked many hundreds of times.

Between 11 January and 20 April, the day I arrived in Helmsley, other celebrated figures to pass away included Alan Rickman, Terry Wogan, Johan Cruyff and Ronnie Corbett. That evening in Helmsley, I heard about the death of Victoria Wood, whose 1980s work (particularly ‘As Seen On TV’) I was a huge fan of. She was younger than all of the aforementioned; she was the same age as my mother; this seemed to come right out of the blue and hit me harder than any celebrity death since perhaps Douglas Adams (49) in 2001. The following morning, as I prepared for day 1, Shaun Keaveny closed his breakfast show with this. Neither of us could remotely have conceived what his show would have to cope with just 24 hours later.

Day 1 (Thursday 21 April)

The Cleveland Way is an ideal trail to choose as your first long-distance walk. Beginning in the quaint market town of Helmsley, it winds its way through attractive countryside, with the climbs not being too demanding until you hit the moorlands above Huthwaite Green on day three. The second half is a coastal walk including three of the North East’s most renowned resorts. Below is the marker post in Helmsley, showing the total distance to the end of the trail in Filey.


Thursday 21st April was a scorching hot day, which could easily have been mistaken for 21st June. And I was over-dressed and over-packed. This is the first thing a long distance walker should learn: pack light. If you’re anything like me you may need to learn it again a year later (see Coast to Coast!).

I left the marker post at 10:35, and reached the first real landmark, Rievaulx Abbey, about 45 minutes later. My main memory of the first part of the walk is a hugely irritating left shoulder strap, which kept slipping down, rendering my load uneven as well as too heavy. Such are the trials and tribulations of inexperienced long distance walkers. Stopped for lunch in the small village of Cold Kirby; downloaded the Victoria Wood song linked above. At 2:10 I reached the official end of Stage 1, the top of Sutton Bank. This is a huge escarpment which overlooks the Vale of Mowbray to the west – drivers may be familiar with the 25% climb from foot to head. On the way to my accommodation I took some photos of the White Horse of Kilburn, which in all honesty is more impressive seen from a distance than close up. Checked in at 3:30 – enjoyed my long bath but to be honest you couldn’t have a much easier first day of a long distance walk than this. Just don’t make it hard for yourself in 25+ degree heat by over-packing.

“Sometimes It Snows In April”

I was born in 1972. I own all of David Bowie’s peak period albums from 1969-80, and mourned his loss, but I always felt at one remove from that particular collective grief. Nevertheless, I asked myself this question the time – “of all popular music artists, which would be your Bowie, your Lennon, your Elvis? Whose death would you grieve hardest, particularly if it was untimely?” I always came to the same answer. It was Prince.

Some time around 4:30pm, still upset about Victoria Wood, I put the words (bad language alert) “fuck 2016” into Twitter. Within minutes I had learned that the greatest pop music artist of my lifetime, Prince, had died at the age of 57. From an overdose of painkillers, apparently – though I should say at this point that (just as with Michael Jackson) the cause of death was of infinitesimal relevance to me and remains so to this day. I have never really understood society’s prurience with regard to the life of an icon, and one listen to ‘When Doves Cry’, ‘Let’s Go Crazy’ or ‘1999’, is time better spent than reading tabloid crap.

Once the numbness had started to wear off and I had begun to accept the awful truth, listening to his music in my room is pretty much what I did all night. The song I played most was this one. OK, it was obvious to anyone who calls themselves a fan. Lauren Laverne was one of many who tweeted its title straight away. The closing track on his most stylistically diverse (and imo most underrated) single album, ‘Parade’, it’s an exquisite meditation on the tragedy of dying young. Its closing couplet is, for me, as perfect as McCartney’s “the love you take/is equal to the love you make” from ‘Abbey Road’. Received wisdom suggests Bowie was consciously writing his own epitaph with ‘Blackstar’ – Prince had unwittingly done something similar 30 years before his death.

Day 2 (Friday 22 April)

Morning: Keaveny and then Laverne did full justice to the passing of a genius, in much the same way as they had done three months earlier. Stayed around to listen until 11, before getting on with the task in hand. Weather warm again, though with a bit more cloud and breeze. The worst part of the day was climbing next to a 1 in 4 road, just to reach the main route again. Did I say something about packing light? Probably.

Anyway, day two of the Cleveland Way is reasonably comfortable again. The landscape becomes more remote as you cross Black Hambleton – this is a long but very shallow climb followed by a steeper (but very manageable) descent towards Osmotherley. Arrived in the village at 4 and checked in to the YHA an hour later. At my age, finding you’re in a dorm on your own (without paying the private supplement) is a bonus. Particularly if you’re overdressed for the weather and your clothes are a bit sweaty. Hey, no-one ever claimed that distance walking was glamorous. After a decent enough evening meal and beer, I listened to a Prince documentary on 6 Music.

Day 3 (Saturday 23 April)

For my money (and I’ve done it twice now) this must be one of the most satisfying and exhilarating single day walks on any national trail/long distance route. A steady climb out of Osmotherley becomes tougher as you ascend Beacon Hill and pass the transmitter. This is followed by a descent to Scarth Nick and a well-marked path to Huthwaite Green (via a short road stretch). Then the adventure truly begins as you climb to the summit of Round Hill and find yourself on the moors. The real ‘fun’ – the source of your eventual exhilaration – is the steep descents and ascents which follow. From Round Hill you cross Faceby Bank and descend Carlton Bank. At this point, there were flurries of very cold hail, in stark contrast to the brightness of the morning. At least I was no longer over-dressed. You then pass the Lord’s Seat café before ascending to Cringle Moor, where you find this…


The Alec Falconer Memorial Seat, Cringle Moor

and you can see all this…


Roseberry Topping (C), Middlesbrough (L) and the North Sea (horizon)

Then it’s down, and up again to Cold Moor, then down again and back up to the Wainstones (see link in summary of accommodation above) and Hasty Bank. Another half hour and you descend for the final time, to the car park at Clay Bank Top. You can be picked up and driven to your accommodation from here. The whole walk is only around 11 miles, but it feels longer, it has great variation and you should feel a real sense of achievement and well-being at the end. If you don’t, you’re probably in the wrong game.

This was the high point of the Cleveland Way: the day I truly caught the long-distance walking bug (and in spite of the travails to come, I never lost it).  A really challenging, adventurous day with spectacular views, variety in weather, more people on the route (hitherto very quiet) and a very knowledgable hotelier to speak to at the end.  The constant round of ascent and descent on steep, uneven stepped paths over four summits in 3.5 miles was tough, but I would not have swapped it for anything back home.  The key moment for me was getting into the bath at the Wainstones just as the football results were coming in on my iPhone radio, with a meal and bed to come, and thinking “this is a grand life”. In a phone call to my mum, I described my walking boots as “my best friends”.

Day 4 (Sunday 24 April)

I spoke too soon. This should have been another splendid day: 20 miles incorporating more moorland summits (including the topological as opposed to ontological high point of the Cleveland Way), Captain Cook’s Monument and – if I felt like it – Roseberry Topping. However:

Within 10 minutes of being dropped off at Clay Bank Top, climbing to Urra Moor, I had to stop due to painful friction on my left Achilles. I’d owned the boots for a year and they had long been broken in; this was the first time they hadn’t felt spot on. Applied a blister pad, but within the hour my left instep had started to complain. Of my two “best friends”, the right boot continued to feel like a silk slipper while the left now resembled a clog with a vice applied to it. The only (marginal) relief came when I loosened my laces, and there were about 15 miles still to walk. You know that in the LEJoG Pre-Amble I say that you’ve really got to want it? It’s because of moments like this.

I stopped for snacks in Kildale, which could have been my destination had accommodation been available. Instead I pressed on to the Cook Monument, where I had lunch. In spite of a disheartening climb to Great Ayton Moor, I forced myself to scale Roseberry Topping. It’s so inviting, you see. Look at that shape. Even if you’ve walked 14 miles, have 6 to go and are not enjoying yourself a great deal, it just demands to be climbed. The reward is my header image for the ‘Sidetracks’ page in the main menu. After that, the rest of the walk was a piece of cake, the only bind being a short ascent past farmland to Guisborough Forest.

Day 5 (Monday 25 April)

My parents bought a small house in the Cleveland fishing village of Skinningrove just over a decade ago. The village is right on the Cleveland Way, and so the opportunity for one day of free accommodation was never going to be passed up. They were at work, so I had the house to myself. Getting there was straightforward enough: just 8 miles, starting with a sharp climb out of Slapewath, then largely flat inland walking to Skelton and on to the coast at Saltburn. Finally, the first 2-3 miles (of around 50) along the East coast.

I checked out in the first rain of the week: there were showers and sunny intervals for the rest of the walk. The high winds on the coast were a harbinger for day 6… there was a gale warning for Skinningrove on Tuesday and some very low temperatures forecast for the Yorkshire coastal resorts that constituted all my remaining stops. On the plus side for today, I washed and dried all my gear. On the minus side, I couldn’t sleep until 3am.

Day 6 (Tuesday 26 April)

Rose at 9am, 16 miles planned, blister pads on the left instep, Achilles, big and little toes, wanting the weather forecasters to be wrong. They were not.

Remember the 25 degree heat in Helmsley just five days ago? Now, on “England’s driest coast” I was confronted with very strong winds, driving rain, horizontal hail and ice crystals. Oh, and sea spray. For some inexplicable reason I had set off without wearing my waterproof trousers, and after a mere half an hour I stopped to put them on. Approaching Rock Cliff near Boulby, the highest point on the East coast of England, was my lowest point of the walk. Stumbling into headwinds, my breathing didn’t feel comfortable and I genuinely thought I would have to give up. Already there was no way I would make the 16 miles to my accommodation in Whitby, so it was time for bargaining: 13 miles to Sandsend was my new target, relying on a bus/taxi to get to Whitby and back.

Fortunately the weather was kinder after Boulby, the wind subsiding just enough, rain easing off and temperatures rising. By Staithes it was actually warm again, and my lunch stop on Runswick Bay beach was quite pleasant. The climb from the beach up to High Cliff was the toughest of the coastal stretch. I was in Sandsend by 4:30 and Whitby (by bus) for 5:40.

Whitby was the place I was most looking forward to staying in. However, it was a bitterly cold evening – once I’d eaten (fish and chips, obviously), the rain came down heavily and didn’t relent. Yorkshire TV was reporting unseasonably low temperatures throughout the region, and even some of the white stuff upon Roseberry Topping.

I guess sometimes it really does snow in April.

Day 7 (Wednesday 27 April)

Excellent £6 breakfast at the HQ of Discovery Apartments on Silver Street. More rain as soon as I was out of my flat – an old lady at the bus stop said the last few days’ weather had been worse than anything Whitby saw all winter. The morning was bitterly cold again, and whole day was wet and grey, at least until I arrived in Robin Hood’s Bay. I spent some time looking around Whitby Abbey, but conditions were not designed for tourism. Obvious photo opportunities though:


Another Cook monument, this one with statue


Whitby Abbey, framed in the Whalebone Arch

This was only a 10-miler, even with the extra 3 miles from Sandsend to Whitby, so I was under a warm shower by mid-afternoon. The sun came out later – easily the best weather since day two. Continued to learn about the ways in which distance walking changes your outlook in subtle ways: usually I am not the sort of Brit who makes small talk about the weather, yet here I am mentioning it every day. It becomes an unavoidable preoccupation on the road.

There was some good news today (actually yesterday, but I didn’t see the news until today). The Hillsborough inquest returned a verdict of unlawful killing, and the jury decided that the behaviour of fans did not contribute to the disaster.

And the sun shines now.

Day 8 (Thursday 28 April)

A long day, second only to day 4. The standard distance from Robin Hood’s Bay to the North Bay of Scarborough (near where my hostel is situated) is 13 miles, or 14 to the Corner. I added 2 from the Corner to the Spa in order to cut the final day’s mileage on a day where I had to catch a train.

I write this almost three years later as a veteran of the South West Coast Path, so it seems strange that the nature of coastal walking once came as a surprise. But yes, back in April 2016, I recall being infuriated by the number of times you have to descend and ascend, sometimes quite steeply. A mere coastal stream or inlet could be sufficient cause for you to trudge slowly down anything from a couple of dozen to well over a hundred steps, and then almost immediately have to climb back to your original height. Rivers, now I expected those to be significant. But doing the same over and again for water courses barely adequate to supply a small campsite, that was galling. And that’s what today was about. Hayburn Wyke was the most arduous, but there was also Boggle Hole, Stoupe Bank and four in quick succession around Cloughton Wyke. This, along with the extreme care needed on the ubiquitous uneven stone steps, made the coastal section more difficult than expected.

The weather started off bright and warm, becoming cooler and cloudier after Ravenscar. By Scarborough it was raining again, and the wait for my taxi from the Spa was excruciatingly cold. The hostel was very basic; sharing a room with a couple of retired chaps, one of whom was touring England on a bus pass and had been commissioned by the Leicester Mercury to interview as many people as he could about Leicester City’s imminent Premier League title. I never got round to asking him whether he’d promised to interview anyone in his underpants.

Day 9 (Friday 29 April)

A short and reasonably straightforward final stage, where you are able to stay on top of the cliffs for the vast majority of the walk. But man it was cold. And this buffoon chose today to leave his gloves behind in the hostel. Pretty certain that the temperature in Filey was in the low single figures Centigrade. When I arrived at the closing marker post (1:10), I wanted to take more photos than I did, really drink in the moment when I finished my first long distance walk. But it was bitterly cold, and a large group of very serious looking male walkers arrived from the other direction after a couple of minutes. Here are my photographic souvenirs though:


110 miles completed


In Filey station, I changed my clothes and re-packed the rucksack in a small cubicle, barely able to move my hands and wrists due to the cold. Didn’t feel any warmth until I’d had some parsnip soup, scone, tea and Drambuie while passing the time before my train. Even on the train I had my jacket zipped up and my sleeves rolled over my wrist all the way home. The last three miles took an hour due to signal failures.


Even if April was not necessarily its cruellest month, 2016 would go on to be one of the most relentlessly cruel of years. It was summed up for many by this picture, which went viral in December:


The cruelty of it all is perhaps best illustrated by the fact that this picture looked somewhat different only a few days before the end of the year. Then we heard that George Michael had died, aged only 53, on Christmas Day. You can try and leave a space here to reflect on the appalling irony, but why not just say it – George Michael is literally the only man to sing on both the biggest selling Christmas no.1 in UK history and the biggest selling Christmas no.2 in UK history (the latter of which he also wrote, of course). A mere two days later, eleven days after the US release of a film that closed on a CGI image of her 20-year-old self saying the word “hope“, and a projection of the late Carrie Fisher was added to the foreground.

As with Prince, Victoria Wood and Caroline Aherne, these were shocking, untimely, numbing deaths. I don’t think my generation was expecting to say goodbye to such huge presences for at least twenty years, and certainly not all in the same calendar year. I write this, incidentally, as someone who in 1997 remained almost completely unaffected by the most famous outpouring of collective grief in modern British history. I can’t really analyse why this felt so different; I can only describe the effect 2016 had on me, and why it is important to this blog.

And for that, I return to the personal, and to my grandmother. When I was in the depths of depression, in 2007, she sent me a simple little card which I still have in my bedroom drawer. It might strike some as “a bit Hallmark”:

Strength Will Come With Each New Day

You don’t think you’ll get through this

Your world’s been ripped apart

How can you ever laugh again

With this aching in your heart

It’s happened for a reason

Believe me, you’ll get through

And when it does, believe me

You’ll be a stronger person too.

But here’s why it doesn’t feel trite or sentimental to me. I deeply regret that, for most of her last ten years with us, my grandmother had to see my all-consuming mental anguish, shame, self-hatred and everything else that came with the breakdown and its aftermath. All that, instead of the joys of building a family of my own. But at the exact point things started looking up again – when I found out I had got my current job – she was the first person I told.

I have never forgotten the light in her eyes in that moment.

Two weeks after I completed the Cleveland Way, the family went to Tarn Hows in the Lake District. This is where my grandmother had asked us to scatter her ashes. It would have been her 84th birthday. Later that weekend I had the idea of walking from Land’s End to John O’Groats and asked my family if they thought I could achieve it.

I look back now and think that the whole idea was born of two things. First, the personal and collective grief that tells you to live out what’s inside instead of dreaming about it. And second, the light in my grandmother’s eyes, that told me I had survived the worst of the darkness and I was still loved. That if I could endure all that April snow, there was surely a thaw coming.

And June could still be beautiful.

Picture shows stock image (gui00878), used in Prince tribute at on 27 April 2016.

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