The Long Read: Cycling The Isle Of Wight

In the first of a series of posts, I look back over this year’s summer of cycling that took me and ‘a bike called Wanda‘ to Spain and Portugal preceded by a short visit to the Isle of Wight. Indeed it is on England’s largest island where we begin…

Distance and topography are two things about which cyclists tend to obsess a little more than your average traveller. I know that my route from home to work is roughly 8km and that it will take me about half an hour to get there. As I live at the top of a hill, I also know that the effort involved in returning home in the evening is significantly more than that required in the morning. Whenever I venture further afield on my bicycle, this knowledge of my daily commute – and other familiar journeys – is put to use in a subliminal fashion to calculate the time and effort required. Should I choose to cycle to York tomorrow afternoon, I don’t need Google Maps to tell me how long it will take and how hard it will be. I’m usually correct. More or less…

Unfolding my Ordnance Survey map on the Red Funnel ferry from Southampton to the Isle of Wight, I discovered that I had a problem. The diamond shape in front of me, detached from the mainland, with Cowes at the top, Ventnor to the bottom, Bembridge in the east, Freshwater in the west and Newport in the centre had me scratching my head. How long would it take me to cycle to The Needles? Would I have the time to get to my campsite at Brighstone before nightfall? Was I being too ambitious in being able to get back to East Cowes in time for my ferry the day after tomorrow? There can’t be that many hills, can there? It’s the Isle of Wight for goodness sake… With few, if any, familiar points of reference, those subliminal calculations were failing me. I looked up from the map, blanked out the noise of the engine, the shouting children and the barking dogs, and stared at the approaching island. To the east and to the west, a thin slither of land stretched out into the distance behind the haze of a summer afternoon. It looked a bit bigger and a bit hillier than I had imagined. Or, come to think of it, not imagined.

Approaching the busy port of Cowes on the Red Funnel ferry

The limited formalities of disembarking done and the River Medina crossed via the short chain ferry, I was soon climbing out of Cowes and heading in a vaguely westerly direction. The plan was to cycle anti-clockwise and I knew of the existence of an ‘around-the-island’ route so was on the lookout for signs. It was only a matter of minutes before I found the first ones and it would be these metallic guides which would dictate my path for much of the afternoon.

Clockwise or anticlockwise? Make your choice…

With route-finding – hopefully successfully – subcontracted out to the boys in blue (and white), I kept cycling. First impressions were good; at times, exceptional. Under an almost cloudless sky of blue – it was clearly the theme of the day – the gently rolling landscape of the north-western quarter of the diamond island was quickly being devoured by Wanda’s fat tyres. The sea came in and out of shot as my journey ebbed and flowed beside the coast along the quiet roads and lanes. On a practical level, it was almost disconcerting cycling on a road surface in Britain that wasn’t riddled with potholes and, as my confidence in the road builders of the Isle of Wight increased, I began to dwell instead upon the at-times-bucolic countryside surrounding me.

Look! No potholes…

This being a beautiful day in late summer, the foreground was often strewn with the rolled-up bales that the farmers had been up since dawn creating, putting into practice the old adage that they should make hay while the sun shined. It certainly was and they certainly were. In the distance, however, was a looming edifice of land cloaked mysteriously in the sea mists of the English Channel. Clearly as my journey continued into the late afternoon, the challenge would be just as much vertical as it was horizontal if I held any ambition – and I did – of seeing The Needles.

Hay bales and distant mist

Sustenance was perhaps needed and it was delivered in timely fashion in Yarmouth where the round-the-island cycle route could be reluctantly abandoned in preference to a disused railway line stretching south as far as Freshwater. The best such ‘greenways’ – and there are an increasing number from which to choose across the country, continent and indeed the entire globe – are those where the paraphernalia of the railway has been left intact and repurposed for modern-day walkers and cyclists. In this respect, the Yarmouth path excelled in the form of the Off The Rails café and, should you not have turned up on a one in the first place, the adjoining Wight Cycle Hire shop.

A well placed café…
…and a beautiful cycle beside the River Yar

The climbing could not be delayed any further and upon turning right at Freshwater Bay a modest amount of effort was required to come within eyesight of the chalk stacks of The Needles and their lighthouse at the westernmost point of the island. The ‘attraction’ for me was looking to the west and the beginnings of the setting of the sun rather than to the east and a giant plastic dinosaur. The less said about that, the better. In fairness, it did seem much more popular with the children screaming back in its direction every time it roared.

The Needles but don’t turn around…

On this first day of the trip, all that remained was to find my campsite for the evening so I re-joined the cycle route at Freshwater Bay, climbed the long hill that had been spotted earlier in the day shrouded in the mists of the sea before a flat cycle to a cliffside pitch at Brighstone’s Grange Farm Campsite. There, between incidental chats with the neighbours, I tucked into some well-earned and gloriously calorific pasta as I watched the sun make its final journey towards the Americas.

Day 1 had been a modest 51km of cycling (the full route details can be found here). Day 2 would turn out to be slightly longer coming in at just over 60km as my journey continued along the southern coast of the Isle of Wight before doubling back towards Newport and a campsite near Cowes.

The day started with the sun hiding behind those cooling sea mists that had been a feature, albeit from a distance, on day 1. Leaving Wanda to stand guard beside the drying tent I spent a leisurely half hour or so sitting on the heavily pebbled beach listening to the sea crash into the shore. It had been this sound that had lulled me to sleep the previous evening as I lay in my tent at the top of the cliff. Come the morning, it was gently lulling me back to life in the most diplomatic of fashions.

A gentle awakening

Having already deviated slightly from the path of the round-the-island cycle route on day 1 in order to access the campsite, I continued to cycle along the coastal A3055 ‘Military Road’ in the direction of the southern tip of the island. I had thought that all the serious uphill cycling had been done on the approach to The Needles the previous afternoon but there was more to come. Shortly after the blue and white cycling route signs began to appear once again near the village of Chale, the road started climbing steeply and I reached the physical summit of my visit to the Isle of Wight at some 175 metres. The day before, my altitude had only ever been measured in two digits but here I was, within an hour or so of setting off on day 2, reaching heights almost double those of the cycle towards The Needles. My thoughts from the ferry were ringing in my ears There can’t be that many hills, can there? It’s the Isle of Wight for goodness sake… Clearly there were.

As is almost always the case, the reward is presented when you stop pedalling, turn around and take a look back at the view and to where you started.

A misty view over Chale

I was now beginning to get the measure – literally – of the island and, looking at my map, guessed correctly that it was perhaps time to take my foot off the accelerator and adopt a steadier pace. Not that I’d been rushing up to this point, but I had been very conscious of the cycling space-time continuum. Returning to Cowes by the end of the day didn’t seem so much of a challenge as I had perceived it upon arrival from the mainland. Indeed, in discussion with a small group of fellow cyclists later in the day, it was revealed that it’s perfectly feasible to cycle the entire perimeter of the island in four or five hours. Not at the pace that I was travelling I hasten to add but, if you did have a ferry booked at either end of the day, you weren’t really at any risk of having to swim back to Portsmouth or Southampton.

In Wroxall, I did what I had done in Yarmouth the previous afternoon in moving off the round-the-island route and onto another of the island’s disused railway lines. This time it had a name – the Red Squirrel Route – and it would guide me all the way to Newport later in the day. Once again, much was being made of its railway heritage with the signs suggesting you might be on the London Underground rather than the Isle of Wight Overground.

No red squirrels were harmed in the making of this film, or even seen…

Arriving in Shanklin, I fathomed a route that had me hugging the coast as far as Sandown. The hustle and bustle of the busy seaside towns was a minor shock to the senses after so much of the previous 24 hours having been spent on quiet country lanes and cycle paths. At this halfway point of my cycle back to Cowes, however, with the heat of the August sun beating down like it had rarely done in the previous three months of ‘summer’, the cooling sea breeze was welcome.

Watch out, cyclist about

Even more welcome was another perfectly located café shortly after the Red Squirrel Trail reverted to following the track of the disused railway. This time, the theme was cycling itself in the shape of Pedallers Café. It was tempting to indulge in one of the sizeable dishes being served up to the other customers but, with a good number of kilometres still to ride, this pedaller restricted himself to a cheese scone and all the trimmings. Needless to say, a few kilometres further down the track, I was wishing I’d opted for double portions…

Peddlers Café

The return to Cowes via Newport was a little like the walk home from the cinema after having seen a great film. It was relatively uneventful compared to the previous day and a half of exploration but allowed my mind to process what I had just witnessed. Far from being a (dare I say?) boring, flat island stuck in the 1950s, I had discovered a beautiful jewel – suitably diamond-shaped – in the English Channel with top quality cycling infrastructure and a place that wasn’t without – in a very positive sense – its cycling challenges.

Upon arrival at the quiet Comforts Farm Campsite later in the day I lay back on the grass satisfied in the knowledge that my two days exploring the Isle of Wight had been time well spent and kilometres very well cycled. After a couple of pints at the suitably named Travellers Joy just up the road from where I’d pitched the tent I was happy in the knowledge that even if Spain and Portugal were ever to disappoint*, I would have at least one cracking cycling memory to look back upon from the summer of 2019. And I hadn’t even had to risk the potentially choppy waters of the Bay of Biscay to get there. Just the rather-more-sedate ripples of the Solent…

(*They didn’t!)

Full details of my route on day 2 can be found here.

Helly Hansen - Ski Free

I travelled to the Isle of Wight at the invitation of Visit Isle of Wight. Much more information about travelling to the island and what you can do when you get there – including cycling of course – can be found on their website,

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