Is it better for everyone to look at a 7 o'clock start? Let's see who else might be on for this and liaise on this thread tomorrow.
Just twiddle up Dark Hill. If it proves too much, don't walk but stop completely, catch your breath, and pretend there is something wrong with your bike until the coast is clear
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Wait until you are ready to go and then twiddle some more. Then at the top you can say you cycled up it for the first time! Job done; next time it'll be easier.
Next: clockwise and Bastard.