please empty your brain below

If going to Guildford Castle, make sure you plan to do many other things in and around Guildford as well. Such as museum, Cathedral, Long Walk along the Way and you'll still have time for other things.
Are you measuring from the Greater London boundary ?

dg writes: Yes.
Upnor Castle is a nice little one, with some pretty walks around the area. Public transport not too wonderful, and it's far less spectacular than relatively-close Rochester.
@Malcolm. Yes, Rochester is spectacular and somewhat underrated I would say. The views over the Cathedral and Medway are amazing. Well worth a trip out.
I really do have to make it out to Rochester one of these days. Everyone seems to like it.

My personal favourite that's convenient to London (though not remotely close - just on an easy train journey even though it must be over 40 miles) is Arundel.
For those less keen to travel and more happy to be completely underwhelmed, try a visit to Bennet's Castle Lane in Dagenham.

dg writes: But that's in London.
(see Sunday's comments)

I almost once lived in a flat next door to Rochester Castle yet have never visited the castle.
The flat was creepy - probably haunted.
DG: Your mission is to visit Upnor (and the remains of the explosives depot)
It's easy to forget how close some of those places are to London. Hever, for example, feels really remote and in the "proper" countryside.

A bit further out, but still easy to get to, Colchester castle is well worth a visit too.
If you ask me Rochester Castle is the best in the list...
@Mikey C

I agree, I was really surprised to see from this list how close Hever is to London!
Hever's appeal can be reduced somewhat if visiting on a day when the Gatwick flightpath is almost directly overhead.
To be fair, Hever is 16 miles from Bromley, and 25 miles from Charing Cross, but the Greater London boundary goes a long way out.
Upnor Castle – built out of bits of Rochester Castle**:

“…theis shalbe to signifye unto you her Majesty’s pleasure that you shall cause such quantytie of stone and brycke to be taken of the old walles and ruynes of Rochester Castle as you shall finde to be of use and fytte to be employed for the finishing of the worckes at Upnore Castle…”††

What comes around goes around.

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