| Day | Route | Mileage | Approx time |
| 1 | Helmsley to Kilburn | 11.3 | 5 hours |
| 2 | Kilburn to Osmotherley | 15.2 | 7 hours |
| 3 | Osmotherley to Clay Bank | 12.2 | 7 hours |
| 4 | Clay Bank to Gribdale Gate (Great Ayton) | 15 | 7 hours |
| 5 | Gribdale Gate to Saltburn by the Sea | 12.2 | 6.5 hours |
| 6 | Saltburn by the Sea to Runswick Bay | 13.4 | 7 hours |
| 7 | Runswick Bay to Robin Hood’s Bay | 16.4 | 7.75 hours |
| 8 | Robin Hood’s Bay to Scarborough | 16.4 | 8 hours |
| 9 | Scarborough to Filey | 9 | 4.5 hours |
After months of deliberation, I plucked up the courage to do a long distance walking trail on my own. I wanted to give myself a challenge, have an adventure, spend time in nature with space to contemplate the surroundings, as well as life.
I researched the route, decided the distances I would walk each day and then booked the accommodation, a combination of B&Bs, hotels and pubs. I had to make a financial commitment, to pay for something, so I couldn’t back out. As this was my first solo multi-day walk, it was a big deal and I dithered for ages before taking the plunge. Once I had taken the first step, I knew it was really happening and I became excited to set out and accomplish this feat.
I chose the Cleveland Way as I wanted to do a trail that was a little less visited than others, so it wouldn’t be busy. I didn’t want to be surrounded by too many other hikers or cyclists. I wanted to be able to feel what it was like in the wilderness alone for several successive days.
The Cleveland Way is a 110 mile long trail in a horseshoe shape around the North Yorks Moors and then South along the Yorkshire coast.
I had difficulty sleeping the night before I set off, with the anticipation and trepidation of starting the walk all on my own. It was exciting and nerve racking in equal measure. After being dropped off in Helmsley I began the walk. I settled into the sound of just me and my surroundings: my regular footfall on the track, my poles clicking the gravel, the rustle of my trouser legs, a whisper of a gentle breeze and an abundance of bird song.
The terrain included stony paths through fields, wide bridleways alongside cultivated fields and some impressive dense woods with the musty smell of damp undergrowth and leaves.
After around 4 hours without seeing a single person, I arrived at Sutton Bank where there were jaw-dropping views over the valley. I was now joined by couples, families and even school parties, all there for the fantastic, far-reaching views.
Before descending to the village of Kilburn to stay the night, I watched a few light aircraft take off, circle around the White Horse carved into the hillside, and then land.
On this day the views were continuously breath-taking. Having climbed up to Sutton Bank early in the morning, the trail remained up high on the ridge all day. I was presented with great expanses of space and uninterrupted views. I was so happy up there. Walking along Sutton Bank I listened to the constant song of the skylarks in the long grasses and I watched the butterflies fluttering amongst the wild flowers.
The extraordinary views seemed to go on forever. The first part of the day I was on top of the world looking out for miles and miles over the valley. This continued as I stepped onto the open moorland. The landscape became more barren with thistles, heather and the gentle rhythm of the grasshopper song. It was so tranquil and soothing. Apart from the very occasional cyclist or walker, it was just me and this expanse of wild countryside. I felt very small, alone in this vast land, yet joyous and so alive.
This was the toughest day of the whole trail, following a chain of moors, each one separated by a steep-sided valley into which I had to descend before ascending the next one. There were periods of the day on lofty ridges again, which made my heart sing. It was blowy on high, feeling wild and remote. The numerous ascents were strenuous, but each climb was rewarded with sumptuous views.
This stretch of the walk is shared with the Coast to Coast trail, which meant I came across many more walkers than the previous two days. I enjoyed the camaraderie of a shared journey and comparing notes with other like-minded hikers. Between these fleeting meetings I strode on, alone and free.
The final climb of the day was up to the Wainstones, a magnificent set of rock crags, which requires a tricky scramble through them. From here there were stunning panoramic views of the surrounding heather moorland and the patchwork of fields below the dramatic cliffs.
It was already 21°C when I was ascending the first hill of the day, so I knew the heat would affect my progress. After passing a couple of people, I was alone once more amongst the ferns, grasses, moors and sheep, the welcoming sound and touch of the wind increasing in strength as I gained height.
The destination of the first climb was Carr Ridge. The path followed this ridge through Urra Moor, finally arriving at the trig point at the top of Round Hill. This marked the top of the moor and also the highest point of the Cleveland Way at 454m. I paused to take in the view, which was a stunning 360° panorama.
As I continued the rhythm of walking alone, carrying everything I needed on my back, day after day, felt liberating. The amazing scenery had ceased to take my breath away, but became standard, expected. I reminded myself how lucky I was to be there and what a great decision it was to do it on my own. Thoughts whirled around in my head as my legs moved progressively and evenly without effort or consciousness.
I was tempted to stop for the day as I headed into Kildale, gazing towards the lush cultivated farmland. I was suffering a huge energy dip, due to the intense heat. But I pressed on with heavy legs, shallow breath, lumbering up and down a couple more hills, before finally arriving exhausted at Gribdale Gate.
It was an even hotter day today as I headed out to Newton Moor where there were close-up views of Roseberry Topping, a distinctive and iconic hill, with a fin like shape. I decided not to hike the extra steep 45 minutes up Roseberry Topping, as I knew the walk would be tough and long enough already in the intense heat.
After another climb up to High Cliff, with panoramic views, the Cleveland Way turned off north-eastwards and I caught my first glimpse of the sea, where today’s walk would end.
I was constantly looking for shade. The temperature soared to 28°C and walking was very challenging in the bright glare of the sun. I needed regular breaks and gallons of water and sought out large trees, so I could rest under the heavy boughs to rehydrate and get my breath back.
After seeing my first adder, startling me from its position in the middle of a wide track, and slithering away to hide, I arrived at Slapwath. This was the first time I had seen a major road for 4 days. I continued my trek towards the sea, with a slight breeze emerging as I advanced. I made it to the coast after an arduous day. A fellow walker had said to me in the pub the previous night, “Walking a long distance path is like life: continuous ups and downs, in gradient, weather, terrain. We just have to keep going ……” Yes, I kept going and was now over half way.
From Saltburn, the path would take a much different feel. There was no longer that remote, detached feeling of the Moors, but more people en route and civilisation at regular intervals.
After a lull in spirits in crowded, stifling Saltburn, I felt a renewed vigour and lease of life as I left it behind and climbed onto the cliffs. In spite of several ascents, the walking conditions were much more bearable, with a light breeze, and splendid coastal scenes.
Sometimes I was elated, taking in the views, breathing in the fresh air, smelling the sea, the plants and the animal life. At others, I was plodding on almost mechanically with no reaction to my surroundings, as it had become normal, routine, unvaried.
Do we always crave newness, change, variety, entertainment, delight? What happens when that initial excitement and wonder at where you are fades and it becomes routine instead of thrilling. Is this a metaphor for life? Those experiences with high intensity, high pleasure, excitement and appreciation are fleeting and over too soon. Then you are left with the conventional, the everyday, the usual.
In spite of these thoughts I was appreciating the entire experience, walking, making progress, being outside every day, living a simple life. It was not always high excitement, but it gave me constant satisfaction.
I was delighted when I saw my hotel for the night, situated high on the clifftop with a bird’s eye view of Runswick Bay from the beer garden. I swam in the cool waters of the North Sea, my clammy skin soothed and refreshed. Later, as I sat perched on the clifftop, beer in hand, gazing at the magnificence around me, my faith in the walk was restored. There would always be these magical moments and you never knew when they would occur. All I had to do was to move forwards and persevere.
As the days went on I became more and more tired. I found myself just walking along in a meditative daze. I was on autopilot. My body was doing the same thing it had been doing for the last six days, putting one step in front of another, day after day. The flat and downward sections were easily achievable, but the hills became harder and harder.
I got to the stage where I was playing games with myself. I set myself a minimum number of miles I had to walk until I was allowed to stop. Or I set a destination marker that I had to get to – a clifftop, a village, a beach, or just a landmark I had spotted from the distance. I thought that without these milestones I would never cover today’s 16.5 miles, this being the longest distance so far.
After a clifftop climb out of Runswick Bay and a few miles walking up high, the path descended to the coastal resort of Sandsend. The route then continued along the A174 for around 3 miles into Whitby, a pretty coastal resort, that definitely attracts the crowds. The narrow, cobbled streets were teaming with tourists. It was sweltering and the hoards made it difficult to pass through quickly. I was a little grumpy being back to the reality of busy roads and crowds. I was yearning for the Moors, for the remote, empty spaces, with quiet and headroom to feel and be with nature.
I passed through quickly and found myself on a spectacular section of undulating paths, which was busy, a popular section for day hikers. I finally stumbled into Robin Hood’s Bay, hot and exhausted and looking forward to meeting my sister and her partner who were joining me for dinner and to walk the next day.
This was a day of contrasts: alone on wild, tranquil, breezy clifftops versus crammed amongst a throng of people in stifling, bustling seaside resorts.
I started the day with a stroll to the Boggle Hole YHA where I took in the phenomenal spectacle of Robin Hood’s Bay. It was low tide when we started walking so we stayed on the beach until the rocky headland below Ravenscar. We spotted some of the large seal population in this area lying on rocks, resting between plunges into the sea to hunt for fish.
Spending the first part of the walk on the beach meant there was an enormous climb up to the very top of the 600 ft cliff in one go. You can see why Ravenscar never took off as a resort, with the only access to the sea by way of this steep, uneven climb to a rocky beach. After in excess of 90 consecutive miles, my tired legs were sluggish as I headed up with leaden steps.
After a busy day yesterday, I was pleased to be back on relatively quiet clifftops again. We followed cultivated fields on one side and sweeping coastal views on the other. It was another day of intense heat and still air. The walking continued to be challenging with several more bumpy descents and ascents. I love walking alone, but having company today was a welcome change. I was distracted from my exhaustion and I kept up with a faster pace than I would otherwise have achieved.
At the end of the walk we landed on Scarborough’s North Bay where we cooled down by immersing ourselves in the refreshing waters of the North Sea.
This was a relatively short hop, compared to the previous days. There was more cloud cover and walking in the cool felt comfortable. My pace increased, I needed fewer rests and it was only 9.5 miles to the large stone carved seat which marks the end of the Cleveland Way.
The first part of the walk went along the sea front in Scarborough, it was gently undulating with a climb out of Scarborough, another up to Osgodby, and then down to the sweeping Cayton Bay. After the short climb out of Cayton Bay the trail descended very gradually all the way to Filey.
After I had taken my obligatory photos to mark the end of the walk, I wandered into Filey with a heavy heart. I had loved walking every day, being out in nature, savouring wonderful vistas, meeting likeminded people, keeping moving. Alongside the feeling of excitement, achievement and pride at successfully completing the challenge, I was feeling a little low and apprehensive about returning back to normal life.
| Drive to York |
| Lift to Helmsley (45 minutes) |
| Or bus York to Helmsley (31X Reliance Buses) – 1 hour 20 minutes |
| Walk from Helmsley to Filey |
| Train Filey to York via Seamer – 1 hour: Filey to Seamer, Northern – 10 minutes, Seamer to York, Transpennine Express – 45 minutes |
| Kilburn | The Forrester’s Arms, The Square, Kilburn YO61 4AH (excellent) |
| Osmotherley | Dale View (Airbnb), 8 Oswaldene, Osmotherley DL6 3AD (excellent) |
| Great Broughton | Wainstones Hotel, 31 High St, Great Broughton TS9 7EW (excellent) |
| Great Ayton | Royal Oak, 123 High St, Great Ayton, Middlesbrough TS9 6BW (excellent) |
| Saltburn-by-the-Sea | Victoria Pub, 3-5 Dundas St E, Saltburn-by-the-Sea TS12 1AH (wouldn’t go back) |
| Runswick Bay | Cliffemount Hotel, Bank Top Ln, Runswick TS13 5JF (good – fantastic view) |
| Robin Hood’s Bay | The Villa, Station Rd, Robin Hood’s Bay, Whitby YO22 4RA (excellent) |
| Scarborough | Caspians Boutique, 6 West Square, Scarborough YO11 1TW (terrible, avoid) |
