please empty your brain below

Rye? No you did that in 2008!
Oh wait - Salisbury's a city.
"Hopefully there'll be decent mobile reception" - Newbury?
The combination of sport and transport made me think Rugby but 'if my connection holds' suggests somewhere on a branch line, which would rule Rugby out. Henley-on-Thames?
Has to be Slough.
Henley sounds right to me. 1h8m from Paddington with a change matches the clues.
Its a tricky one, this.

I wondered about Portsmouth or Southampton, and with anybody else the term "town" wouldn't have been deliberate, but with DG I suspect every word counts.

I then thought about places on the Isle of White, which would require a connection, albeit to a ferry. Cowes might fit the bill, but it's more like two hours from London and would hardly be considered as "not a small town" - also, Who goes to Cowes in January, unless to sail?

And then I remembered that it was meant to be in the South East anyway, and none of those really count. So, I thought I would wait and see.

I hope it's not Dover seeing as the train service is knackered due to the sea wall collapse!
Another vote for Henley
OK, I'm here and it's pretty. Let me walk around for a bit, and I'll report back.
Trouble with Henley on Thames is that it's not very obscure. Most people could place it on a map, or at least get the right river! The same would go for Marlow.

My first guess is Lymington. Felixstowe is a bit short of history.

Many of the suggestions above have direct trains from London. I don't think DG would change trains unnecessarily, just to confuse us. But he didn't say the connection was onto another train, so it could be somewhere stationless.
Malcolm, I like the idea of Felixstowe, specifically catching the Ferry from Harwich, not sure if it runs in the winter and its well over an hour from London.

Anyway I'm with Robert, just gonna wait and see. Intrigued tho 'cos seems dg has been everywhere on south coast and anywhere else coastal is more than an hour away (oh, perhaps Frinton). So thinking it might be somewhere non coastal. Is if Henley on Thames?
I originally thought of Newmarket, which is about an hour from Kings Cross via Cambridge, but I'm not sure it has much waterside.

Henley seems possible. It's about an hour, with a change, from Paddington, but rather more from Bow! And has little of transport interest as far as I am aware.

Weybridge has the Thames and the Wey Navigation (for waterside) and Brooklands (for the motorsport, aviation and bus museums) and it is one change from Stratford (at Waterloo).

Thanks to Victorian competition and good fortune in the Beeching era nearly every large town in Kent has two independent rail routes to London. Despite the blockage between there and Folkestone, you can still get to Dover, using the Chatham route.

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