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I've got two boys at Judd. Waltz in and tell them you talked to someone on lfgss with kids at the school. They'll roll out the red carpet for you and your Garmin.
Alternatively, there are plenty of open days and evenings. I'll give you the nod if I see anything suitable before the forum goes tits up.
Somerhill indeed. When leaving, I found that you can get in easily through the A21 entrance (saw another runner come in that way), but I came in from Tudeley Rd by the main castle - tbf, nobody around, so that was also pretty easy.
You can easily get all the Tonbridge School squares just by walking around the pitches - they allow you to do that, even if you're just walking the dog. There's a public right of way coming in from London Rd. Judd School is my big issue - there's a square fully in their grounds that is majorly blocking my square growth, but they lock up tight.