Ive done a handfull of the 1000km Longest day rides in varying weather conditions with riders i know well and enjoyed most of them, my first one i did i was not prepared well at all and it was a loooong horrible day / evening learnt lots about prep that day. The furthest so far was 1220kms a couple years back that was a tough day , 11 or so hours of mostly cold rain and a only a few hours sunny dry conditions (Cheers Nelson) .
But it is always good to catch up with the other riders at the finish and see what route they had done and how their day was.
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