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I've been on were led by Martyn Roach (google if you don't recognise the name), and he made a practice of refusing to say where he was going. He said he was working on a "need to know basis" - for example - "we're turning left in 100 yards".
Sounds like a great idea. Would be well up for this. My life is far too planned. 60miles secret clubman route.
The difficulty of doing the full distance does depend quite a bit on the conditions on the day.
Apart from rain (and we don't really want to expose our ancient kit to a lot of water and grit) there's wind direction. If I'm doubtful of my ability to get to a certain point and then return without undue suffering, I don't like a tail wind on the outward leg; I like an easier return trip - it's so much better for morale!
That's one reason why I'm not keen on riders having gadgets pre set to a specific route.
It's worth adding that the best (hard) rides I've been on were led by Martyn Roach (google if you don't recognise the name), and he made a practice of refusing to say where he was going. He said he was working on a "need to know basis" - for example - "we're turning left in 100 yards". The pupose of this was, I think, to stop riders suddenly remembering 'important social engagements' when they realised they would have to deal with a tough climb.