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I was in a similar position to you before going out to Italy this year and riding Monte Grappa with no real experience of long climbs. In the weeks before leaving I'd ride out to my nearest hill (High Beach) do it like ten times and then go home. It worked pretty good. But then I wasn't trying to keep up with Bert.
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This may have been covered, but how do you get flagged? Does another rider have to do it?