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@Greenbank
180km one way.
360km riding back to London Fields (saves you the hassle of getting the train).
I'll be getting the train out to Leatherhead to start at about 6pm, going through to Dunwich, turn around and come back along the same route. I'll then be carrying on through London Fields to Putney to make it up to 400km.
What to do depends on what you're comfortable with. My first 200km ride almost killed me. There's no way I could have considered doing another 200km straight after it. Now it's a relative walk in the park (physically) but it'll never be anything but mentally challenging.
My first long fixed ride was 162km. My second long fixed ride was 315km several months later. Both were fine given that I'd done plenty of 200km rides in between.
Consdiser the "double distance" rule of thumb. If you're planning to do a ride of X miles then you need to have done at least one of X/2 miles. Follow this and you should finish, you might be fucked at the end of it, but you should finish unless you're a big jessie. So 50-60 miles so far and you'll get through the 100 mile DD. Mind you, plenty of people ignore this and are fine. I know someone who's first ride over 100 miles was a very hilly 385 mile Audax.