Big Issue Foundation

From Dungeness to Durness to support Big Issue vendors 

John Simmons took on an epic 900 mile cycling challenge for his 60th birthday.

John Simmons recently cycled from Dungeness to Durness (D2D) for his 60th birthday in support of The Big Issue Foundation.  

For John’s 50th, he cycled from Land’s End to John O’Groats (LEJOG). Since 10 years have passed, he decided to do something similar for this milestone as well.  

The trip from Dungeness to Durness (all the way to the northwest tip of the mainland at Cape Wrath) took him 14 days (not including rest days), was a total of 907 miles, and had a total ascent of 39,927ft! 

John decided this milestone trip would support The Big Issue Foundation because “given the wrong set of circumstances, anyone can end up homeless”.  John has exceeded his initial target of £2,000 by raising £2,810 on his JustGiving page so far. 

John kept everyone in the loop with daily updates of his adventure and what an adventure it turned out to be! 

John before kicking off on his journey


  • I started my trip in Dungeness at the old lighthouse (pictured above). 
  • It was a cool and grey day, but very dry. 
  • The 50 miles from Dungeness to Rochester were (thankfully) completed without incident. 
  • This first day was really a warmup day as the 70+ milers started on Day 2 with the journey to Cambridge. 


  • On day 2, I completed 74 miles from Rochester in Kent to Trumpington just south of Cambridge. 
  • I crossed the Thames using the Gravesend-Tilbury passenger ferry. 20 miles took me nearly 4 hours. 
  • Went from Gravesend, a lovely town (and the burial place of Pocahontas), to Tilbury. 
  • I saw Audley End House near Saffron Walden. It was once the largest private house in England, but now it’s reduced to a third of the size of 500 years ago. 
  • Weather was pretty good – I was even able to wear shorts for most of the trip! 


  • On day 3, it was 71 miles of long, straight, flat roads with a light tailwind. 
  • Cambridge city centre on a sunny Sunday morning was beautiful. 
  • The 10-mile cycleway alongside the guided bus route to St Ives merits a special mention, passing through some lovely (albeit flat) wetland areas. 
Taking in the sights – Audley End House near Saffron Walden


  • Day 4 was 67 miles also of long, straight, flat roads but with a moderate tailwind. 
  • The total climb from day 3 and 4 was 3,000 ft. 
  • The Lincolnshire wolds was a lovely rolling ride on quiet minor roads with good tarmac. 
  • I then took the National Cycle Network (NCN) route 1. There was an off-road section past Humberside airport that was wonderful, and The Bridle Path self-service café deserves an honourable mention with their honesty box that must have had £40 of change. 


  • Day 5 was a bit longer at 83 miles and a total of 9 hours from door to door.  
  • East Yorkshire was an exceedingly dull county to cycle through and the day was a bit of a blur. 
  • I had to weave through the Samaritans signs to get to Yorkshire via the Humber Bridge. This route was OK, but not as spectacular as cycling the Severn Bridge. 
  • Having meandered backwards and forwards over the A63 a few times I crossed it one last time near the point it morphs into the M62. This can take you all the way to Liverpool, but I’d be more inclined to stop at Manchester. 
  • The bits of East Yorkshire I passed on the 83-mile slog were flattish, dull and boring. Minor East Yorkshire roads appear to be wider and faster than many of the A roads that I’d travelled to date. Market Weighton, Pocklington and Easingwold, were the not very high highlights, before crossing the A1.  
  • I passed Stamford Bridge then was on to Masham where I promptly cycled past the campsite as the signs only faced one way. 


  • I had been looking forward to this day most as a trip highlight.  
  • While relatively easy on paper with 56 miles, it included Tan Hill, the point where the route crosses the Pennine Way, and the location of the highest pub in England. The hill was 12 miles and 1250 ft uphill, and all into a vicious headwind.  
  • The long downhill was great, however. The ride was then completed by 15 miles of rolling hills.  
  • I passed through Appleby-in-Westmorland and on to the campsite at Long Marton. 
  • The day was a total of 56 miles and 4000ft of uphill completed.  
  • My average speed for day 6 was just 9mph, so by far this was the slowest day. 
Gandalf the cat disrupting John’s route planning


  • Day 7 didn’t start off great as my Big Issue cycling top and one sock fell in the dog’s water bowl just before I set off for the day. Luckily, it turned itself around and day 7 ended up being wonderful and easy.  
  • There was a light tail wind and bright skies with occasional sunny intervals, so I was flying along the relatively flat lands between the Lakes and the Cumbrian Fells.  
  • I passed through the village of Unthank then sat on a bench by the river in Carlisle where I had some snacks. Carlisle, surprisingly, was a pleasure to go through.  
  • Next came Scotland, via a few miles of my LEJOG route of ten years previous. I didn’t revisit this route again until the bridge over the Moray Firth at Inverness.  
  • The rest of the day saw more gently rolling hills all the way to Hoddom Cross. 
  • 60 miles done at nearly 12mph. 


  • Day 8 was 72 miles across some remarkably wildernessy bits of Dumfries and Galloway.  
  • Then onto Ayrshire, which passed pretty uneventfully, so not much else to say about day 8. 


  • Day 9 began with an early start at 7am to catch the 9:30am ferry. 
  • After cycling 25 miles to the ferry, it broke down after 5 minutes in harbour and I had to wait 90 minutes for the next one. 
  • The 25 miles to the ferry was actually very enjoyable. I passed Prestwich airport, wildlife reserves, rivers and endless golf courses in the Troon area. Plus, at Ardrossan I saw the (proper) sea for the first time since leaving Dungeness. 
  • Arran was a wonderful island to cycle around! I spent about 60 miles mostly hugging the coast. It has only one BIG hill and I only needed to cycle a small portion of the island. 
  • After 15 miles I was off Arran and back to the mainland via the Lochranza to Claonaig ferry. 
  • After this, there was only another 35 miles to a village near the Crinan canal, Scotland’s Panama in miniature. It was remarkably pretty, and I had a wonderful pub meal in the village of Tayvallich. 
  • Of course, I arrived late to the campsite due to the ferry breaking down and having to catch the later one. 
  • Day 9 was a long day with 88 miles that included that big climb on Arran, but this did also at least include the 18 or so miles by ferry. 
Long roads ahead but beautiful scenery

DAY 10

  • Originally, I planned to take Loch Awe Road but was warned by the campsite owner the night before that it strikes terror into even the most experienced hill climb cyclists. Naturally, I decided to just take the coast road via Oban instead.  
  • There were still plenty of hills but lovely views of jura and mull instead of the conifers I would have seen on the inland route. 
  • I then went over the Connel Bridge and onto the cycle path before I finished for the day at Creagan.
  • Day 10 ended up being only a bit over 50 miles. 

DAY 11

  • Day 11 had been looming over me for a while. At 78 miles it was close to the longest mileage day of the whole trip, with the added joy of the biggest climb of the trip right after already doing 64 miles.  
  • These 78 miles were made harder by accidentally going on the wrong side of Caledonian canal at one point.  
  • Rather than being on the cycle path, I was on a footpath and had to lift my bike over several gates and a fallen tree. 
  • I then switched to the nearby B road where I had 10 miles of ups and downs and twisty turns, all while looking down on the straight and flat bridleway. Rather than brave the forestry track that runs alongside Loch Lochy, I reverted to the A82 via the Commando Memorial at Spean Bridge.  
  • From Laggan I followed old railway lines and the canal towpath to Fort Augustus. These tracks weren’t bad quality, but they still hurt your backside on a touring bike. 
  • After all this, I climbed 1200ft (4 miles) of big hills (with no walking!). But what a view from the top! This was then immediately followed by 10 miles of almost constant down to the campsite on the quiet south shore of Loch Ness. 

DAY 12

  • This was originally supposed to be a short day. However, I decided that if I pushed on, I could get all the way to Durness the next day, which would make getting to the Cape Wrath ferry much easier the day after. It thus turned into another killer day because I quickly realised that day 11 had taken a bigger toll than I realised. 
  • The initial, mainly flat, run to Inverness was lovely. Inverness had presented navigational challenges when I did LEJOG, and so it did again, not least because one side of the bridge over the Moray Firth was shut. This necessitated a circuit of Inverness Cally Thistle’s football ground; another bucket item list ticked.  
  • The rest of the day was a blur, with significant stretches of headwind and a 700ft, 8-mile climb at the two-thirds point. 
  • As a plus, however, our last-minute camping spot proved to be the best camping location of the whole trip; Falls of Shin, just south of Lairg. This is also apparently the best spot in Scotland to see wild salmon jumping! 
John’s bike being mobbed by a flock of sheep

DAY 13

  • The route of day 13 was mostly north with a hint of north-east.  
  • The 5 miles to Lairg were a joy. I followed the river and passed a rope bridge that was signed to Lairg railway station. Then there was just a long stretch to Altnaharra. 
  • Before Altnaharra I passed, and frequented, The Crask Inn. This made Tan Hill look positively cosmopolitan; there is nothing else within 10 miles! Here, I had my FIRST bacon butty of the trip. 
  • I then took a minor road to get me to the north coast. It was 21 miles of almost nothing but amazing scenery, a Broch, perhaps 6 cars, and 10 miles of headwind, in which I pedalled downhill all the way.  

DAY 14

  • The last day was dull and overcast, but at least NOT raining.  
  • Cape Wrath is the most northwest point of the UK mainland and was not easy to get to as you need to cross the Kyle of Durness by the little motorboat ferry. 
  • After being mobbed by a sheep flock departure party (pictured above), my bike was lifted into the boat and off we went.  
  • My first impression of the route was that it was, indeed, bad. What I saw turned out to be amongst the better bits. After 2 hours (12 miles), I got there! 
  • The place was about as bleak as bleak can be, but I’d done it, which genuinely did tick a bucket list item.  
  • My bike was genuinely suffering at the end, and the trip back finally finished off the front axle. 
John’s proof that he and his bike made it to Durness

John’s concluding thoughts on the trip were that while he will never do the D2D trip again, he will undoubtedly be doing another multi-day cycling trip. So, we’ll be keeping an eye out for his next milestone trip! 

John also included some useful stats to either convince or deter (you choose) anyone from doing the trip: 

  • Total number of miles: 907 
  • Miles per day: 67 
  • Average cycling per day: 6.5 hours 
  • Vertical ascent: 39,927ft 
  • Biggest individual hill: The climb out of Fort Augustus, on General Wade’s Old Military Road, the B862, about 1200ft in 4 miles.  
  • Steepest hill: 15% (On day 1 up the North Downs in Kent) 
  • Hardest hill: Tan Hill in the Pennines (day 6). Was 12 miles uphill with a height gain of 1150ft. Wasn’t really steep, but there was a strong headwind all the way up. 
  • Highest point reached: Tan Hill (1911ft). 
  • Fastest speed: 41mph 
  • Total time spent cycling in the rain: 25 minutes. 

It sounds like John had… well… a time. But we’re glad John made it in one piece and we’re so grateful he decided to do this trip in support of The Big Issue Foundation!  

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