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@gbj_tester
Ay, and there's the rub. Picking the right gear for Windsor Hill is probably the way to go, but you need to do several full-effort test rides to refine it. I've only raced up there once, and after a few tests on different gears on my road bike, I settled on 42/21 fixed for my race, and came an impressive dead last. While I was waiting for the start having got there much too early I watched Rob English ride up about 10 times for training, and then he won it in 1:35 on his road bike.
http://www.maidenheadcc.org.uk/results.2005/tt051016.htm