The Rollin’ 100 is a newly introduced one hundred mile ultra marathon, taking place in and around the hills of Shropshire, a county which borders both England and Wales. 2025 was the event’s inaugural year, and I was really excited to run it, not having run in these hills before.
However earlier this year, my plans quickly went from this “this shouldn’t be a problem” to, “I’m not sure I can run this”. It’s been a bumpy ride for me since early March in terms of my running. Around this time, I developed discomfort in my achilles tendon and it took me a while to realise something more serious was up.
Long story short, I had to massively cut back my running volume, and introduce a daily physio rehab routine in mid-April. This gave me about 10 weeks to rehabiliate and simultaneously try to hang on to fitness for the Rollin’ 100.
Rollin’ 100 – my tail of risk versus reward
As the event date loomed closer, I realised I was at a decision point. It was now a case of risk versus reward. The daily rehab my physio had me doing was really helping and he seemed to think I could do the distance. However, my weekly long runs I built back up to being just capable of doing in late May were flaring up my achilles around 25-50% of the time. During, or the day after my weekend long run, my achilles would ache a little.
I realised that if I were to attempt the Rollin’ 100, I may very well end up with pain or discomfort in the achilles, and that I would need to quite possibly choose between forcing through, or giving up.
With all the daily rehab work I had done, and the insane number of simple, boring training loops I had done on my nearby local trails to keep things simple and the variables under control, I decided I would risk worsening my situation in an attempt to complete the 100 mile race.
My goal simply became: “Can I finish a 100 mile ultra marathon in a reasonable amount of time, with an on-going achilles tendinopathy?”
In hindsight that was kind of a stupid idea, but I seem to be drawn to challenges where the outcome is unknown. Matter of fact, I think it’s a common trait in ultra runners; most of us actively seek out lofty goals or difficult scenarios.




The Rollin’ 100 pre-race experience
I drove to Shropshire a day before the event and stayed at a very basic and simple AirBNB cabin, just 10 minutes away from Bishop’s Castle (where the race starts and ends).
My hosts were very friendly and the cabin itself was great, simple and a bit dated, but it was clean and had everything I needed. Even better, it was nestled on a quiet hill in the midst of a large section of forestry. The only noise to worry about was the wind whistling through the surrounding trees. Perfect for what should have been a good night’s rest.
I did manage to get decent enough sleep. My nerves were high based on the prospect of running 100 miles the next day, so it wasn’t perfect, and even though I was in bed at 9pm, it only felt like I finally nodded off around midnight.
I was up at 4:30am to ensure I got my breakfast, electrolytes and morning routine sorted before race registration between 5 and 6am.
Registration was at a rugby club, and was simple enough. I just need to pin on my racing bib number and have my GPS tracker attached to my pack. Katie and Alan, the organisers and race directors of Runningmonk Trail Events, along with the volunteers kept everything running smoothly.
There was a bit of light drizzle, but temperatures were warm enough once moving, so I was a bit indecisive on whether to wear my Odlo shirt, or a more open and cooler Salomon running vest. Finally I settled on the Odlo shirt, but later on the vest would have been a better choice as it turned out to be a very humid and warm day.
As everyone was ready to go, we started 10 minutes early at 06h20.
My pacing plan
My pacing strategy was to try and maximise distance earlier on while my legs and body were fresher, but without going out too fast and potentially aggrevating my achilles.
I used my ultra pace calculator tool to set a linear progressive pacing strategy of 10%. That is, start 10% faster than average goal pace, and finish 10% slower.
From the start I ran pretty comfortably, sticking with a group of people roughly running my ideal pace. Together we sat somewhere around the top 5-10. However, bear in mind this was a small race, so there were around 35 people in total. Two or three shot off a fair bit quicker, with one or two of those eventually dropping out.
From the get-go I found myself running alongside a chap by the name of Luke. It turns out we would stick together and run 90 miles of the race together!
The route
The first 10 miles front loaded around 600 meters of elevation gain, as we made our way towards Long Mynd (Long Mountain). The Long Mynd is a heath and moorland plateau that forms part of the Shropshire Hills in Shropshire, England.
Once on top of the plateau, we had panoramic views of the hills around us, and also found our first aid station and checkpoint.
I only spent two minutes here, grabbing some salty crisps, a few biscuits, a slice or two of orange, and refilling my water.


We soon entered a gulley leading down into a valley, which meant a rocky and technical descent from the plateau. It’s an absolutely beautiful part of the course with streams running alongside the technical trails all the way to the bottom where you meet the nearby town of Church Stretton.

I won’t go into painfully long detail about all the sections of the course, but rather summarise the Rollin’ 100 into sections.
Mostly all trail with some road sections, especially when coming off major trails such as the Offa’s Dyke or Mortimer trails and entering towns and small quaint villages. The route lives up to it’s name – rolling! There are plenty of hills.


Offa’s Dyke
The Offa’s Dyke trail doesn’t refer to the slang word, but in this case means a ‘wall’. Basically there is this massive linear ‘earthwork’ that roughly follows the border between England and Wales. The official full length trail is around 176 miles in length.
When we ran on this trail, we were either running alongside this large earthwork, or at times on top of it. I didn’t get any photos as much of the time I was on this section was at night.
There was about 6 miles (10km) of this trail at night where we got attacked by large swarms of literally hundreds of flies. I managed to inhale them twice, and Luke was bitten multiple times. Next time I’m there I’ll definitely bring a ‘midgie net’ for my head. They were attracted to our head torches.
Mortimer trail
The Mortimer trail was very overgrown in parts. If I had known the extent I would have worn long leggings even through the humid evening we were on the trail.
Picture ferns higher than your head and completely enclosing the narrow single track trail, interspersed with masses of thick bramble that cut your shins and thighs over and over again. Then, to add insult to injury, every now and then you hit patches of stinging nettle.
There was also a woodland section on this trail with steep sideways camber where you needed to duck and dodge thorned branches that were growing across. A local runner out running joined us on this section. She was wearing thick, knee high running socks. By the end of that section we wished we had done the same.
I’m pretty sure she had a good chuckle after meeting us. Luke and I were cursing the whole way through, and at one point I let out an exceptionally crude expletive when a bramble hooked me on the top of my head and yanked me back as it stopped my momentum.
I was promised this trail will be cut back next year, so if you’re reading this and planning on doing the race in 2026, don’t worry (but maybe wear 3/4 length running leggings just in case!)
In hindsight the difficulty of this section is a good memory of some tough, yet amusing moments in the race.
Towns and villages
The towns and villages were beautiful. We saw a couple of spectacular castles, with a checkpoint at one of them. One of the ladies running in the race whom I had run a short recce with in May had kindly offered to buy a batch of delicious fresh baked cinnamon buns and got them delivered to this checkpoint. (Thanks Laura!) I saved mine for around the half way mark and had it with a coffee.
Woodlands
There were plenty of woodlands and forest along the route too. Steep climbs, steep downs, rivers, and a few difficult to navigate forks in the trail.
At one point Luke and I ended up somehow running into someone’s back garden. It was massive, and quite overgrown, just off the trail, but was at a point where we were meant to turn. We stumbled through, finding ourselves on a series of cascading decks with ponds, and eventually hit their border fence. We decided to climb the fence as the prospect of going back through their nettled garden didn’t appeal.
Thankfully the correct trail was just over their fence. We found out later than one or two other runners had done the same.
Checkpoints and volunteers
The checkpoints were well spaced out. I think the longest section without one was maybe 20km. The volunteers were all so friendly and helpful. Everyone jumped into action as soon as we would arrive, refilling water and bringing us anything we needed.
The checkpoints from the drop bag aid station (just over half way) and onward all tended to have hot food and drinks.
My favourite checkpoint on the Rollin’ 100 was one at night, I’m guessing around 11pm. They offered us chilli or leek and potato soup. Luke and I had just been talking about favourite foods in a race about an hour before and both agreed potato and leek soup was a winner. As the lady offered us this choice our eyes lit up. It was destined to be.
I found myself spending more and more time at checkpoints as the race went on. My idea of 5 minutes max at every checkpoint quickly went out the window. I spent around 2.5 hours total over the race sitting in checkpoints, which massively affected my overall time. It’s something I really need to figure out for these longer events, as I would like to be much more efficient.
Pace, durability, and pain
I ran well up until about 90-100km in. At this point my durability really dropped off. Everything was hurting now, but especially the outside of my right knee. Every time I slowed down it would hurt, but running on it also hurt. A constant cycle of pain which I recall starting around midnight.
I took two paracetamols which helped for a few hours, but they wore off eventually. I had to push myself through the pain for another 10 hours to cover off the remaining 70km or so.
Morning, and remembering the chafe
Luke and I caught the first light around 4:30am in the morning. It brought on a little bit of a renewed energy.
A little later still we found ourselves in a heavy downpour of rain. It definitely “dampened” the mood, as we thought it might persist all the way to the end. Thankfully it only lasted 45 minutes more.
I was pretty happy after it subsided, since I felt cooled off, and a lot of the salt deposits on my back and sides were washed away.
That’s another side of the pain. Chafe. I’ve dealt with it many times before, but never this bad. Not even the Wild Horse 200 chafe was as bad as this. The warm and humid day and night had meant excess sweat. The salt deposits then caused chafe.
I developed chafe in the all parts of the groin area. And I mean all parts. Then I got it on my sides and back where my pack was rubbing. It stung pretty much all night. I guess we can’t always be lucky with all the variables! Next time I’ll apply more anti-chafe ahead of time.
Final checkpoint
Eventually we hit the final checkpoint. I encouraged Luke to head off without me. I had been slowing him down with my knee pain. Additionally, I wanted to catch up on my hydration for 15 minutes at the checkpoint. We were in joint 4th place and keen to finish together, but I knew I would slow us on the final 18km.
I stumbled out of the checkpoint and ran into Alan and Katie (race directors/organisers). It gave me a nice distraction from the pain of moving again after sitting, and I took that renewed energy and focused on moving as efficiently as I could toward the end.
The last stretch had some challenging climbs and descents. I got a bit lost on one climb, ending up on the wrong side of a barbed wire fence. I had to climb to get back over. Then it happened again, and again. I scaled three barbed wire fences, which I’m sure you can imagine can be quite challenging when your muscles and joints are all seizing up. One of them even had an electric fence wire along the top.
Thankfully I didn’t end up snagged anywhere, and I miraculously avoided being shocked by cattle-strength voltage.
Another harsh camber section and I eventually found myself on mostly flat grassy trail with only 5km left. It was easy running in now, and I picked up the pace, keen to maintain 5th place now as I had the feeling my pace was slower than anyone else behind due the pain I had picked up in my knee.
The final stretch in to the rugby club finish was a relief. I had somehow made it 100 miles, on rough, hilly terrain, with a dodgy achilles tendon too.



At the end I was well looked after. I received my finishers buckle, some Runningmonk Trail event swag (running top + vest), and a massive hug from Alan.
Katie brought me an ice pack to put my achilles up on, and I sat and enjoyed a hot tea while I reflected on the past day of running.
Alan and Katie are a lovely couple. They’ve built an amazing little events company and host some brilliant races and events around Shropshire and Bishop’s Castle. This year was the first year they hosted the Rollin’ 100 miler, and I wish them all the best for next year’s event.
If I don’t have any other new races booked, I’ll certainly be looking to come back and knock a few hours off my time on next year’s Rollin’ 100. This time armed with longer leggings and backup midgie net too!
Haha, of course you had to do this race despite a dodgy Achilles, Sean!! The only sensible thing to do, right?! 😂
What a wild ride! There are so many things that I love about this race – especially that it’s small and family-like and that the route leads through a stunning countryside. Your photos are incredible – what a beautiful, rugged place to run through (and occasionally curse at). Even the nettle/bramble/fern combo sounded awful and somehow funny the way you described it. The garden detours and the barbed wire gymnastics, ha!
So nice that you had Luke running with you most of the time. It must have been hard to let him go ahead and push on your own after that final checkpoint. That took some serious grit! I’m in awe how you pushed through those final miles despite all the pain (especially chafing pain!)
Huge, huge congrats! I hope the Achilles will finally heal up and that you get to do more ultras soon!