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@Greenbank
Porkers 2pm start, so you'd want to be in Poole at 1pm latest I guess.
From Chepstow is jokes. 4 changes and 14 hours to get there before 2pm.
Chepstow (00:08)-> Gloucester (9 hour wait for the 09:37) -> Swindon -> Reading -> Basingrad -> Poole (13:50).
Bath Spa is a lot better, one or two changes. 09:44 from Bath Spa changing at Dorchester (cycle from Dorchester West to Dorchester South) and you get in to Poole at 12:31. 30 mile ride from Chepstow to Bath.
09:00 from Bristol Parkway Station (13 miles from Chepstow) to Bristol Temple Meads (09:13). 09:25 from BTM to Dorchester West (11:40). Dorchester South (12:00) to Poole (12:31).