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OK, I've had a look at this as I've been wanting to do some rides from Tewkesbury for ages.
TLDR; I think it is just about OK. You can book the outbound in advance so it's the return that is the challenge and there are options that I've done before that are easier than the main line, such as going via Evesham/Worcester or Gloucester.
There is a train that connects Evesham and Gloucester via Tewkesbury which says it needs reservations but I doubt it would in practice. But it is rideable from either.
Evesham / Worcester
You can get to Oxford without reservations. There is another line that goes up to Evesham / Worcester (15/20 miles from Tewkesbury) from Oxford. I thought that line might be OK too as I've rocked up and used it in the past) but it says that you do need reservations.Gloucester
I got back from there once by rocking up at Gloucester (10 miles from T) after a DNF (I had res but from Shrewsbury the following day so no use) - nominally that needs reservations but it wasn't a problem to get my bike on.
I reckon the main GWR (Paddington - Reading - Swindon - Bristol - Wales) is a right pain but the other lines / stations are more lenient / less demand for bikes.
I'll let you know if I try it.
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Which station would you go through to get to those? Like, do you train Ealing -> Reading first? Many of the Reading trains don't stop at Ealing or go to Paddington and then back out, but providing you time it ok, and maybe ask organisers for a later start they might work.
Could do part of it on a Friday night carrying camp kit and then wild camp out west but even that seems quite fiddly and requires finding a decent spot, which is shit in England because of the laws. It's one thing for me to sleep in a bivvy bag in a carpark but don't know if the missus is going to be up for that nonsense.
Anyone know of a nice way to get there by train from west London?
All I can come up with is:
Paddington -> Tewks or Ealing -> Reading -> Swindon -> Tewks
GWR trains are shit for bikes with their random 2 bike slots and it'd be Friday just after peak hour so wonder if there's a less stressful way of getting over there. Missus not keen on overnight ride over there.