The Big Isle Be Back Challenge - Isle of Wight Loop - Phil Cox

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We saw Brian before he saw us; sporting his white Isle Be Back Challenge t-shirt standing on the dockside with his hands in his pockets. The last time we had met was at the leg waxing in Wantage the week before. Phil thought it would be a good fund raising opportunity as well as a chance to drum up some publicity for our ride and the charity. Brian made the journey from the Isle of Wight to support the event and watch us get our leg hair removed by Faye from the Indigo Beauty Rooms. A proper job, mine are still silky smooth.

It was good to meet up again although the time spent at the terminal was brief. The clock was most definitely running on this ride, if we had a chance of getting round the island in time to catch the planned ferry we needed to be moving and not talking.

Brian was well prepared and knew the plan; we dumped our rucksacks into his boot and had a quick brief before heading off towards Cowes. The plan called for Brian to drive ahead to crucial junctions and indicate our route; he had taken the time to print a big black arrow to be held up for our benefit.

It was nice to be riding again after the hiatus of the ferry crossing; I was surprised at the amount of recovery in a reasonably short amount of time. The ache in my neck and shoulders returned; on the mainland it had been insidious but now the discomfort came back quickly. At least it wasn’t getting any worse, it was just annoying.

I made a point of yelling out to the Phil and Mark when we passed a pub that I had eaten at during my recent holiday. It would be fair to say that I have eaten at quite a few pubs on the Isle of Wight so it was nothing remarkable. I was slightly embarrassed to realise the garden was full of punters and they had all looked up from their conversations when I had disturbed the peace.

IOW somewhere

Brian met us near Cowes and directed us to a hidden cycle path that would run the length of the River Medina towards Newport. The smooth surface and deserted feel to the path spurred us on; the odd runner and dog walker greeted us along the way but in the main it was free riding. Regrettably, the 10mph speed limit had to be ignored but we did slow down when approaching other path-users.

Newport suddenly appeared as did Brian. The Medina had narrowed down to a dead end dock and mud banks were visible on either side of the water. We took 5 minutes to eat and top up bottles; I had a small pork pie as a change from the sweet food I’d been eating. I have enjoyed pork pies at all sorts of events, mostly days out at cricket but I have been known to sneak the odd one on board for a ride. Phil asked if he could have one but, to my complete dismay, I realised I had only packed one. I was supposed to be good at food but I had failed miserably on this occasion.

We headed up towards Ryde, back on busy streets with building traffic. I’d dropped behind on one of the longish, shallow hills, when I caught up I realised that not all was well. Phil was gathering bits of Go Pro mount from the road after it has sheared off from its handle bar position. He was clearly very miffed, the camera had been a present from his mum and dad specifically to record the ride and now he had no way of mounting it let alone using it for the rest of the ride. Now was not the time for a smart comment, we ground on up the hill. I spoke with Mark about setting his Go Pro to capture our return to Wantage Market Place, at least we could put that footage up on the Facebook page, this would be no consolation to Phil though.


Ryde disappeared behind us to be replaced by Sandown, a fairly nondescript place that is always busy; we pushed on to leave it behind quickly. I was looking forward to Shanklin because it was an area of the Isle of Wight that I knew reasonably well, unfortunately, we approached it from an unfamiliar direction so my ‘local’ knowledge had less value than my pension fund. We pulled up at a T junction by the local church.

‘I can’t see Brian, better give him a call as I haven’t got a clue where I am,’ I mentioned in a low key way.

The advice was to head downhill which required a left turn at the T junction, then look for a car park on the left. After 500 metres or so it didn’t feel right and we weren’t seeing the car park that Brian had mentioned.

Just as we put the phone down for a second time, two local lads tripped over to us offering their assistance. They were definitely street geezers and off their melons on something more than the local ale. They couldn’t stop talking and the delivery was almost too fast to follow.  Given the amount of time we had been up I considered asking them to share some of their gear but soon realised that would be cheating.  Cycling could not cope with another scandal…too soon.

‘Good luck lads, you look like you like a challenge, that hill is a challenge go so good luck yeah man haha woooo.’ Etc., etc., etc. They were genial lads, nothing nasty about them at all and, to be fair, they did point us in the right direction.

We topped the hill and freewheeled down to Brian in the part of Shanklin that I did know. All my favourite places were there: The Rock Shop, The Crab Inn and the Chine. No time to sight-see today though, we had a very brief stop to fill up our bottles and headed out towards Ventnor. Another ride milestone now beckoned; the climb out of Shanklin to Ventnor.

I knew this would be a tough one having driven it a number of times earlier in the year. It’s always the case that climbs appear innocuous from the comfort of a car, and so it was for this hill.  We managed the first steep section out of the town; Brian had parked up in a layby, we pulled over and asked about the rest of the climb.

‘It’s not that far or steep now and then it’s downhill into Ventnor, no worries lads,’ said a deadpan Brian.

As a result of this slightly inaccurate description we now refer to long, tough hills as a ‘Brian hill’. It was hateful and I wanted it to end but it wouldn’t. However, our falsely derived hope got us to the top…just.

Things settled down a touch now as we freewheeled into Ventnor and headed out towards St Lawrence and the Military Road. Lights were required again as it was getting dark quickly. The road surface was a little uneven and we saw evidence of roadside subsidence. One particular stretch had a traffic light control around the slumped roadside. I warned the others about the odd camber in the road as we rode around the cones, I remembered that from our holiday after nearly burying the car in the cliff side.

At this point I was starting to feel the miles we had put in during the day, the thought of getting to the ferry became all-consuming. I cast my mind back to the start of the ride and it seemed a long time ago. We had made a sterling effort to catch up some time but it hadn’t produced the results we were hoping for.  In fact, the penultimate ferry was now out of reach, we would really have to pull the stops out to get the last ferry. It had always been a contingency but I never expected to have to use it.

We faced one last big hill as we climbed up to Freshwater, again it was a nasty one and I was glad to get it done. I was rapidly running out of fuel given the extra push but not yet at the stage where I would have to chance my delicate stomach with an energy gel. Instead of risking a ‘reverse liquid lunch’ I went for a whole ginger cake – down in one! It worked a treat hitting the spot very quickly. Suddenly, Yarmouth terminal appeared and not a moment too soon, we had approximately 20 minutes to spare before the last ferry left.

Brian had been fantastic, his diligence with the route finding had paid off and we were back in one piece. His mum had joined us for the last section but regrettably, we didn’t get a lot of chance to chat. I think we were all starting to suffer given the mounting mileage, chatting seemed to be an extra, unnecessary effort.

Leaving IOW

Not much else to say about the Isle of Wight except that a nice man took our photo’s promising to post them on the ‘What’s on in Yarmouth’ website and Mark caught up with an old school friend who worked on the ferry.  A bizarre coincidence but then this trip was completely out of the ordinary. We could put our feet up for a bit and get a hot coffee on ferry; this left plenty of time to worry about how the last 80 miles would pan out.


Read about the last 80 miles from Lymington to Wantage soon…!!/TheBigIsleBeBackChallenge

Further reading…..

If you liked this blog please take a moment to check out my book describing the solo Land’s End to John O’Groats ride in 2012, all profit from sales to

Please click the cover image for the Kindle version or click here to order a paperback copy. Thank you!


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