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Friday 12thJune
Caerphilly to Chepstow
At 9am we arrived back at Caerphilly Castle - our bikes were securely locked in the guardroom alongside the East Gate and we began our tour of the extensive remains. The first thing which strikes you is the leaning tower - leaning at 10 degrees. Parts of the castle are apparently very similar to that of Tonbridge in Kent - this was built by Richard de Clare, the father of Gilbert de Clare who built most of Caerphilly in the late 13th century. It is also interesting to note that Gilbert, having defeated Simon de Montford at the battle of Evesham in 1265, went on to attack de Montfort's son who had escaped to the castle at Kenilworth with his followers. Kenilworth had huge water defences and took over 6 months to capture - this probably influenced Gilbert in his building of Caerphilly.
Next stop was Newport Castle - it sits right in the middle of the town next to the river and squeezed in between the road and railway bridges - not much remains.
From Newport we travelled the short distance to Caerleon. Even less remains of this castle which now forms part of the boundary wall of a pub overlooking the River Usk. Lunch was taken in the pub carpark overlooking the river.
After Caerleon we made our way in the direction of Chepstow calling in firstly at Penhow Castle. The only viable route was along the main A48 for a few miles, but fortunately there was a cycle path for some of the way and when we ran out of path, the traffic was not too heavy as the motorway runs almost parallel to the road at this point. Penhow is not open to the public and what you can see from the access lane appears to be of fairly recent construction.
Eventually we veered off the main road at the village of Caerwent, otherwise known as the Roman town of Venta Silurum. I believe Time Team have done some digs here recently and there are many Roman remains to be seen throughout the village. 
Just down the road was the village of Caldicot. The castle here was constructed in the 13th century by the de Bohuns (Earls of Hereford). The front gateway was being used by a wedding party as we arrived - so we sneeked past to have a quick look inside. Much of it has been restored by the owners and it is in very good condition.
Our final castle was Chepstow now only 5 miles away - or was it? We passed at least three signposts over the next couple of miles which each told us that Chepstow was 4 miles away - would we ever get there? Chepstow Castle is a grand structure built on the banks of the River Wye not far from its junction with the Severn. Building of the castle was originally started by William FitzOsbern in 1067 with the great tower 
being completed in 1090. William Marshal added further fortifications and it is amazing to see some of the wooden doors surviving from this time.
The mileage at the end of the day was 35.9 miles.
Castles visited - 6 plus the Roman town of Venta Silurum at Caerwent