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@clubman
A very long time ago, in the eighties, I rode a reliability trial, which is what 'sportives' were known as then, called 'The Harp Hilly 100' (that was kilometres by the way).
This was held in February and starting near Amersham went over Bison, Ivinghoe Beacon, and Aston Hill. I rode the event three times and for the first attempt I was foolish enough to use a 64" single free - I did get round eventually, but not within the qualifying time, which I did manage once subsequently, on gears. So my answer to Spencerwells question 'has anyone done it before?' is - yes and no.
But I notice Wayfarer says he does** not **plan to do the hardest climbs to start with.
I hope to be at Amersham station on Saturday.