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@clubman
This sounds like a great project.
For the past few years I've done a pre Christmas ride to my sister in Oxford - nothing compared with this proposal. However even my little trip has proved hard work at times, especially when I failed to leave early enough and got caught in the dark.
Apart from last year (when I went by car because of the snow) the temperature has never been much of a problem, and I've never encountered any ice on the main roads. It's the possibility of a headwind that's the real enemy, and as we know the prevailing wind is South West, so a Westerly is quite a likely possibility. I don't think even in my best years I would have wanted to try this ride into a strong wind.
Therefore I suggest you should have a plan B just in case. Somewhere to stop on the route, an arrangement for a lift, or check up on how to finish the journey by train. Nobody will be very impressed with the thought that you would have been very fit...if you had survived.
A final thought: On Christmas morning 1967 my clubmate Martyn Roach rode from South West London to Newport Pagnall. In 1968 he won the British Best All Rounder Championship.
Good Luck.