Isle of Wight Challenge 106km

Dave and Calvin’s Big Day Out on the Isle of Wight Challenge 106km

Report by Calvin Wright

Firstly, this is a “cathartic” review on my experience, there were many others in the club and other island runners that did this event, and their advice, support and words of wisdom were so helpful. Can I also thank you all for the support before and on the day from club members in person and on online was awesome.

Those of you that know me well will know that each January I have to plan something that will hold my interest for the first six month of the year.

Having received feedback from some random “expert” on Facebook that my IOW to Lands’ end to John O’Groats and back trip last year on a 1998 C90 moped, was not environmentally sensitive and that I wanted to have the annual leave this year to do something similar. I was a bit stumped on what to do for 2024, many of you will also know I have repeatedly said I would never run a marathon again. So how did I end up at Chale showground at 7 am on a pleasant May bank holiday, thinking I had a chance of running around the Isle of Wight.

So why.

If you hang around with the wrong/right people, bad/awesome things can happen.

Having seen the achievements of some other club members in their longer distance running in 2023, and a casual conversation with Tim Nobes on a wet January club run, Tim suggested the Serpent Trial 50km in July 2024. He felt this would be a good challenge for me, and it is 31 miles so technically it is not a marathon and I wouldn’t be breaking my promise to myself of no more marathons. Roll on another week and I had a conversation with someone who said if you’re doing a 50 km race you might as well do a 100km and if you’re doing 100 km you might as well do it on home turf.

So that was it, challenge accepted, with knowledge of my awful ability to procrastinate and end up doing nothing, I went home, signed up, paid my money, and was locked into the challenge.

Accountability buddies

Another random conversation about my talent for losing interest in long term projects, gave me the advice to tell everyone I know that I was doing the challenge. Not to show off but to ensure I would not “bottle it” through losing interest or because I couldn’t be ar*ed to stick to the 16 weeks training plan. (More about that later).

What about the training programme?

So having signed up to the challenge I started to look at training plans, then what I had really signed up to sank in. The training plan was like nothing I had seen before. Big weeks would be 80 miles + and would include a month of Saturday marathons and Sunday long runs and 3 sessions during the week.

How am I going to get this one past my wife?

The age old issue we have as runners is how to convince our none running partners; that 16 weeks of delayed DIY projects, constant talk of training programmes, endless packages of running gear turning up at home and the complete lack of ability to have any meaningful interaction on a Saturday or Sunday because you are either planning your runs, doing your runs or sleeping because of your runs.  Now my long-suffering wife of many years has never stopped me doing anything and is always a supporter of me. But this challenge was on another level. So the conversation was had…….. Me: Darling I’m thinking about running around the island” Wife: Ok, when, Me: July Wife: OK Me: are you sure? there is a massive training plan and it will mean I’m constantly either running or talking about running and I will not get any of the DIY jobs finished, Wife: running is all you talk about and you started the bathroom 5 years ago and it’s still not finished, Me: Is that a yes. Me: oh bugger that means I’m going to have to do it now.

If you’re going to do something you might as well, do it for a reason

Last years moped ride had raised a brilliant amount of money for an island charity and I found it was really helpful for my accountability issues and kept me on track. So this year I decided that the charity my wife works for would be an excellent choice. Not only because of the awesome work the Homestart team/volunteers do for some of the most vulnerable families on the Isle of Wight, but also to help me with the guilt of this rather selfish challenge.

It about the mind as well as the body

All of you that have followed a plan know that the closer you can stick to the plan the better chance you have of success and suffering less.

It is hard to pick out highlights and low lights of the runs on a 16 week training plan as there were so many, including a 45km training run from the tip of Sandown and the coastal path to Brighstone in the grip of one of the many storms we had this year. This lead me to  curl up in a ball at Blackgang carpark and uncontrollably sob to myself and phone my wife for a lift home and cut my run short by 10km, my wife didn’t answer the phone. All I can say is the 10 Km home proved to me that I can keep moving despite everything in my head and body saying stop. The next week I ran a 50 Km and loved every minute of it.


If you are doing any event which has the option for having a tracker. I would said get one, the amount of people that were following me on the day virtually on the island and from all around the world was so helpful when the going got tough. The tracker enabled them to meet us on the route or send messages of support during the day.

One the day

So 6.30am on Saturday 4th May, I found myself in the starting pen of the Isle of Wight challenge, In there were some of the Isle of Wights best club runners and people I have admired for many years. I did have a little moment of “imposter syndrome” but 16 weeks of training said to me I have the credibility of at least being able to turn up at the start.

Dave you are a star.

So many of you will know Dave Cass as a stalwart of our club and someone who I had always admired for his understated awesomeness. We had not planned to run the challenge together but had had a nice time running the Rog run and shared our experiences of the “training plan”. This might account for why we ended together within the first 10km. I can honestly say that Dave was the perfect running partner. We laughed, cried, suffered at different times and together, but at no point did he get grumpy with me and my incessant talking and positivity.

Chale to Isle of Wight Pearl, 10.5 km total time 1hr 19 minutes

The weather up to the challenge had been “changeable” which meant the first leg up to the IOW Pearl was rather wet which led to wet feet and socks from the start. Due to path closures, we went inland and ran about 500 metres from my house, this meant I bumped into my wife taking the dog for its morning walk and some friends from the village had turned up to cheer us on. (What a boost)

The First mini aid station was at the Isle of Wight Pearl this was well stocked with loads of goodies and smiling volunteers and the groups that would follow us round most of the day. We stopped there for 5 minutes, and Kev Winchcombe helped Dave with his knotted tubes in his camelback.

Isle of Wight Pearl to Nodewell Farm total distance 25 km total time 3hrs 30 minutes.

This stretch of the Island coastal path is my favourite and home stomping ground. I will never get tired of the view with the beautiful white cliffs of Tennison down stretched out in front of you. Today the sun was shining, and it was as beautiful as ever. We had a cheeky little detour just before Freshwater that took us up onto the golf course which added a little more elevation but is a much better route to run due to the surface of the path being flat and you’re not 3 feet away from a 300-foot drop. Down the golf course through Freshy bay, more support including a couple of runners from work with a sausage roll for me (well-remembered lads).

As we set off up to the Tennison monument we had the bizarre experience of seeing the park run runners, running back down to freshwater bay. This again was such a treat with loads of clapping cheers from us and the park runners. Along to the coastguard cottages, down towards Alum Bay but branching off to Nodewell farm for a major aid station. By this time the heat of the day was starting to make me feel a lot more tired than I had hoped, we stopped for 10 minutes to top up water, drink flat full fat coke and take on board food.

Nodewell farm to Shalfleet. Total distance 39km and total time 5hrs 37 minutes

The plan was to spend as little time at the aid stations as possible until later in the day, so I set off with a big cheese and ham baguette, planning to eat this as we walked up the next hill toward Headon Warren. I think due to the heat, I took one bite and gagged…..oh bugger that wasn’t part of the plan. Fortunately, the route from there was mainly downhill to the coast and flat until Yarmouth. At Yarmouth view point I remember Dave and me looking at each other and for the first time we saw some doubt in each other’s eyes. This is where I had my first mini melt down, as the utter enormity of the task ahead sank in.

We collected our preverbal Shiz together and went off to play in the mud of Boulder woods. I had been through this session many times over the years and in the training runs for the event and know it would be disgusting. It did not disappoint us. The mud was shin deep at times and just so slippery that you couldn’t stay upright without walking and hanging onto barbed wire fencing. The Shalfleet aid station was in a field just before the little creek bridge and again was well stocked and the volunteers were so nice, smiling and offering to top up water bottles etc. I recognised one the volunteers but couldn’t remember where from, so I asked him, “I work in the hardware department at Hurst’s in Newport” was his answer. I asked him how come he was volunteering at this event, and he said because he wanted to help ordinary people doing extraordinary things. Cue more tears from me.

Shalfleet to County Show Ground. Total distance 53km total time 7hrs 54 minutes time of day 14.52.

I remember leaving Shalfleet station and having a nice chat with Dave about how our legs were starting to hurt. We shared story’s about the “not so good” training runs that we had experienced and this was when the learning we had from those runs was now coming into play. As we came out of the hills and onto the main Shalfleet road we were met by another legend of  Island running who had set out a picnic with his son to watch us all go by. I had run a couple of 50 kms with them 15 years ago and he suggested I looked like sh#t warmed up. Dave laughed and I took it as a compliment from him, and off we went to sample the back roads of Newtown and Porchfield. Just past Newtown my son and his girlfriend were waiting for me, cue more tears as he told me how proud he was of me, but I looked like sh#t. Again Dave laughed, and I took it’s as a compliment. I said to Dave I need some time to myself just to get myself together and he’d tagged up with a couple we had been talking to earlier on in the day. I ran alone for the first time through Parkhurst Forest; my feet were hurting, my legs were hurting, I wasn’t eating and who knew that Parkhurst forest had hills in it. I popped out of the forest onto Noke Common and had another moment. I sat down to try and work out why my feet were hurting so much. As I emptied the mud out of my shoes I realised it was because my socks had blood on them, FFS I never get blisters, cue more tears. Dave came trotting round the corner we gave another one of those looks at each other and set off to find the mid-way point at the county show ground. Just before we got there the two lads from work popped up again with a sausage roll for me, cue more tears.

We ran into the midway point (which is the finish of the 50km option), this place was like rammed with people supporting friends and family, more IOWRR were there to clap us and the others in, cue more tears from me.

Dave and I agreed that we would have 30 minutes max here, I went to get my feet looked at by one of the awesome medics. Three blisters popped and dressed, and two open blisters dressed, sorted, now to eat. The person behind the food counter was the daughter of HOMESTART’s manager, she thanked me for raising money for Home Start I took my chilli and cheese and started crying again. Eating this was so hard it just wouldn’t go down FFS. Dave came and sat with me. We gave each other that look again and in unison said how the F*ck were going to do another 53 km now. But decided that several people had suggested we were awesome during the first 50km so we must be, and awesome people just get on with it.

County Show ground to Oakfield school Total time 11.52 total distance 71 km

Cue the happy smiling face of Ross W, who towed us along the cycle pathway to Newport at 10-minute miles. That was like a shot in the arm for Dave and me, we suddenly felt good again and it seemed possible again. Cue Mrs Cass and her mini aid station at the top of the racecourse with cooled coke. We stopped at Wootton Tescos for ice cream and had to eat it quick while we ran because the sun was still so hot. The stretch along the main road to Ryde I had been dreading because of the traffic. But it was relatively quiet, there were so many people tooting their horns and shouting encouragement from their cars, or just clapping as we ran past them as they went about the life. Up towards Oakfield school we were met by Mr and Mrs Ruth and I was presented with a freshly made Marmite Sandwich, (you will never know how important that sandwich was guys). We rolled into Oakfield school past another Mrs Cass pop up aid station.

Tried to eat some proper food but that wasn’t going down, cue water melon, peanuts and pretzels, awesome smiles from the volunteers. I had my feet looked at again and re-dressed, Dave was on a bit of a high at this point and when we looked at each other we both had a bit of a glint in our eyes; actually finishing this event was a possibility.

Oakfield school to Culver down Total distance 83km total time 13.57

We trotted of in highish spirts becoming accustomed to the constant pain across our bodies and the tiredness too that really starting to set in.

Down through Puckpool park, past people enjoying food and drink in the café, along the sea front and we bumped into the Sharps out for an evening stroll. They wished us good luck and didn’t mention how shit we looked which Dave and I took as a compliment; this was more evidence of how awesome we were. At some point around the back of Bembridge we tipped over the 50-mile mark. We gave each other another look, congratulated each other and I cried a few more tears. Now I’ve been up that hill a few times but never with 50 odd miles in my legs. Cue dry heaving, dizziness and general swearing but no tears (they had all gone by now). We got into Culver aid station at around 9 pm, Jane A, Kev and Gill were there as well as some others Kev pointed out we both looked like shit, Jane and Gill suggested we were awesome and we agreed with all three of them.

Eating was an issue again; I had run the last 13km powered by only peanuts and pretzels so needed to eat something “proper”. They had a pizza oven; I ordered, sat down, put some in my mouth and then put it in the bin, that wasn’t going to work. I settled for chicken cuppa soup with only half the water in it. Bang! the salty goodness gave me a lift. It was getting dark by this time and cold, people in the aid station were shivering I was glad I’d packed and dry long sleeve top and waterproof. Mrs Cass provided Dave with his own pop-up aid station with a full wardrobe. I donated a woolly hat to some guy that was really suffering alone and gave him some of my gels that I can’t eat. It seemed like a nice thing to do and certainly easier than giving him a piggyback to the finish.

Culver to Ventnor Botanicals Total time 17hrs 23 minutes Total distance 97 km

 We rolled out of Culver with a plan to walk down to Yaverland carpark and then see whether we felt like running. We chatted about how awesome we were, then started to suggest that we were considering needle craft as a hobby rather than running. At Yaverland my wife was there waiting for me as we were getting towards midnight this was lovely and a bit of a lift. We put a real shift in along Sandown seafront all the way to Shanklin steps, with two visit from Mrs Cass’s pop up aid station. So the sting in the tail was that, due to Leason Road being closed, we had the treat of Cowlease Hill. Past the duck pond up to the left hand bend and up the footpath/mountain through Shanklin Estate onto Shanklin Down and about 900 foot of climbing in less than a mile. We trudged up there, with the sweet sound of Dave threatening acts of violence to the route planner. While I pointed out the stars in the sky, or it could have been delirium / hallucinations. As we started to drop down to Ventnor via Darkside to the industrial Estate, the marshals asked us to keep an eye out for a lady in front of us as she looked like she was struggling (given the fact we never saw her until the finish, we wondered what they must of said about us to the people behind). Darkside was such hard work on the quads. We both filled the silent night air with threats of violence to the route planner. On arrival at Ventnor aid station at 00.26 hrs Sunday morning we both gave each other a look that we were going to get this, but it wasn’t going to be a sprint finish. Dave visited a porta-loo and I asked the aid station to hide the chairs, so we didn’t get tempted to sit down. They stuck a light on our back packs and off we set.

Ventnor Botanical Gardens to Chale total time 19.21.02 total distance 106 Km (Garmin said 68 miles and 4500 ft of ascent)

Running was out of the question now, I was remembering a podcast I had listened to while training that talked about being in the “pain cave”. So, we set off to Chale, my head was thinking about what needlecraft I could create to make my pain cave a little more pleasant. Chewing on peanuts and listening to Dave discuss with himself how much he was enjoying the experience and how if anyone mentioned running an ultra-again they would meet the same fate as the route planner. The road along the undercliff was just an absolute suffer fest for me and Dave I think. I was about 20 yds ahead of Dave all the way along there, not because I was fitter it was because it hurt too much to walk slower. Every so often I would hear Dave footsteps run up to join me then drop back. I would suggest to Dave he was looking awesome, he suggested it was dark and I couldn’t see him. This happened so many times but it kept us both amused. We thought at one point we had entered the twilight zone as the were no distance markers at 99, 100 and 101 km but it was probably trophy hunters.  As we entered the bottom of Niton hill we were met be two of my friends from the village, my son and his girlfriend. It was 01.30 in the morning what awesome people they are, they all suggested we were superhuman, Dave and I agreed. Up the hill quick left along the cliff path, there were loads of lights in the distance which when we got to them, they were marshals making sure no one left cliff past the stone walk. When we got to Blackgang carpark, I looked at the spot where I had my cry on my 45 km training run and thanked myself for having the experience it was really paying off now. My friends and son etc were there. My friend who had been on a stag do and was rather drunk pointed out to us we had less than a park run to go. Dave and I left the carpark wondering if there would be space for him in the grave next to the route planner. We had our first glimpse of the finish. Lights in the distance welcoming us home, down the slippery, muddy path past the chine park and back of the manor house. Then a cheeky left along to the coastguard cottages and down the rather dodgy cliff path. Just before we entered the finish compound, Dave and I had a man hug, thanked each other, and decided if we were indeed awesome, we should run the last 300 yds.

As we ran family and friends, and Mrs Cass were there to cheer us over the line.

So that was it all done, but little did we know ultra distance is the gift that keeps giving. As I tried to eat some food (crispy bacon and beans) my body went into massive shakes I asked the guys on the table next to me if that was normal and he suggested it was, so I carried on eating my food which tasted of something nice and was looking like it might stay down. As I was leaving (my son gave me a lift home because apparently, I look tired) I saw the guy I had given my hat to at Culver, he was asleep with his face in his plate of beans on the table in front of him. I decided that would be my offering to the ultra-gods and that he could keep my hat.

The days after the run I had trouble sleeping, eating, and kept on randomly bursting into tears. This is normal apparently, I just needed to let it flow over me, book another ultra and I’ll be ok because I am fecking awesome and I know it 😊

Top Tips for get a 100km done.

Find an event, ask others what they have done.

Find a decent training plan and stick to it.

If you start crying on a training run that is good training for the brain.

Training eating proper food on your long training runs.

Expect to not be able to eat the food you have trained with on the day so be open to other stuff.

Surround yourself with people who have done ultra distance running, they will have lived every one of the experiences you will have and tell you it is normal.

Raise some money for charity that work for.

Hire a tracker and give everyone you know the link.

Smile at everyone, it gives you an 8% boost in energy apparently.

Have spare pair of shoes at halfway that are at least half a size up because your feet will swell.

Expect to suffer that’s all part of the game.

Expect to cry a lot.

Expect to look like shit and expect people to tell you.

Expect to have a massive mood dip for the week after.

Sign up to another ultra before you take up needle craft.

Run with Dave because he is a star!