Checkpoint Numbers & Names
Isle of Wight 1 – Freshwater
Isle of Wight 2 – Godshill
Isle of Wight 3 – Culver Down
After a good nights sleep and hearty English breakfast it was time to set off for day two of the ‘Tour de IOW’ and the 4th, 5th, and 6th checkpoints on the island.
Unfortunately there was a minor hiccup as my Garmin steadfastly refused to load in the route I’d planned for the day so I was left with no choice but to do a bit of ‘Freestyling’ and grab a tourist map and plan my ride as I went. Fortunatelt the first checkpoint of the day was in Freshwater bay only a mile or so from where I had stayed the night so it was pretty easy to find that one, and with the obligatory photograph taken and the map consulted it was along the coast road for a few miles before heading inland to Godshill.

So, on leaving Freshwater the coastal road (known as Military Road) takes a steep uphill section which on looking back at the top gave me some great views back across Freshwater and beyond to the Needles point making it well wort the climb. The rolling terrain continued for three or four miles with some great views out to sea on the right and the Isle of Wight Area of Natural Beauty to the left. This continued for a total of ten miles all along the glorious coastline but as I headed through Atherfield in the direction of Blackgang Chine I could feel the road starting to become steeper.
From Atherfield and through Chale the ride up to the peak of Blackgang Chine was as steeper than any climb I’d done on the island so far, and caused me to stop part way up for a breather and a drink and to chat with some walkers who were circumnavigating the island on a walking holiday. After catching my breath and continuing on I eventually weaved my way to the top, and the Blackgang observation point where the walkers were already stopped and taking pictures – it would seem the walking path was more direct and thus a bit quicker than circuitous road route!
From Blackgang my ad-hoc route now took me away from the coast as I cruised downhill through Niton and on to Whitwell where I turned north to head straight to Godshill, which strangely isn’t at the top of a hill. Once in Godshill I had three objectives, find the checkpoint, visit the model village, and buy an ice cream. The model village came first so I stopped off, and the lady on the gate was more than happy to let me stash my bike around the back while I visited the village, which took me around an hour, although I could have spent a lot longer given the time. A few yards after leaving the village I happened upon the chapel that made up the checkpoint, and even better there was a cafe selling ice cream directly across the road from it!

So, after quite literally chilling out for a while it was time to get on the move again and head off to the third and final checkpoint at Culver Down. Not being able to remember the original planned route from Godshill to Culver I consulted the map and decided that the route least likely to get me lost would be through Sandford and in to Shanklin before going along the coast to Culver down.
The road out to Sandford was an ‘A’ road, but in common with many of the road son the island was still much quieter than I was used to so it was a more than pleasant cruise down to Sandford after which the road took a brief uphill turn before continuing downhill right in to Shanklin and the beach. Once I hit the promenade at Shanklin I could see the obelisk and Culver Down way in the distance so decided to ride as far as I could along the coast as I could before going up to the obelisk as I could see that it was at the top of quite a high cliff. After following the promenade as far as I could all through Shanklin and Sandown it was time to head along the road through Yaverland and on to the road that would lead to Culver Down.
Culver Down must be one of the most inappropriately named places on the island – it should be called Culver Up as the road leading to it was ferociously steep, even worse than the earlier climb up Blackgang although for this climb I managed to make it to the top without actually stopping, although I did take a few minutes to look around Bembridge Fort at the top of the hill. Having looked around the fort it was time to jump back on and ride the last half mile to the obelisk / checkpoint. Once at the checkpoint and taken the necessary pictures there was time to stop at the cafe for a cold drink before turning around and cruising back down the hill I had struggled up around thirty minutes earlier.

Conscious that I had a ferry booked back to the mainland for late afternoon I opted to take the main road back from Culver Down to Ryde through Brading, which was pleasant enough, and with Ryde being signposted I didn’t have to worry about going the wrong way, but instead spend the time enjoying the views over the Solent and reflecting on what a great couple of days cycling I’d had and mentally planning my next multi-day cycling route.
Once I got back to Ryde upon checking the timetable I had nearly an hour before the next catamarran to Portsmouth so there was plenty of time for me to have that Fish and Chips that I’d missed out on the night before.
Overall the two days away carrying luggage was pretty successful, and certainly gave me the taste for doing something similar for other quest adventures, especially as nearly all the local checkpoint have now been visited train / B&B questing looks to be the future.
Miles Cycled – 35
Checkpoints Visited – 3
Total Miles Cycled – 1044
Total Checkpoints Visited – 64
Click here to download a gpx file for this ride