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@Sam
Sounds an awesome ride. Big respect to Martin for finding you lot out there in the dark.
Jonny, I'm available on both dates. Funny really, I was hoping to get another Kent ride in before the end of the season, as I'm pondering doing it on my Brompton, for a laugh like. If that were the case, the first route would probably be the one for me, not too hilly (except for Exedown), and as you and Tim know the route I would make sure you wouldn't wait for me should I momentarially become detached from the rear (!).
But it's not my decision, I'll let you decide.