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This sounds like a great route to do, yes, and may sounds like about the right time of year. I doubt I'll get my Simplex Carlton painted and built up in time so will be doing it on Sturmey 3 speed hub (close ratio unless I get a different wheel no less), but assuming I can get it fettled up and not slipping I''m sure I could manage, should be entertaining. I never was much one for spinning anyway, so I'll just have to toughen up and grind my way up those climbs....
I could be up for this (that's to say the ride, not the back injury)
One possibility would be to use part of the Hard Day in January route - a Fairly Easy Day in May.
The route is shown in that thread - I can suggest other cafe stops short of Berinsfield according to the taste and strength of who ever turns up. I'm afraid this does involve asking the participants to come to the west of London to start (Staines), but there is a good train service from Waterloo.
All variations of the route will include some climbing, but I think most of the bikes we would be using have variable gears - even if you are going to put your faith in a Simplex Tour de France! If Gino Bartali could win the Tour (1948) using a Cambio Corsa, I'm confident we should be able to manage in the Chilterns with the kit you have been writing about in this thread - although I think we may give the Christmas Common climb a miss.
It seems to me to be desirable to have a route that finishes where it starts, rather than making the use of a train unavoidable.
Let me know what you think.