The average train between Maidenhead and Chepstow Castle takes 2h 47m and the fastest train takes 2h 3m. There is a train service every few hours from Maidenhead to Chepstow Castle. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.
Trains run hourly between Maidenhead and Chepstow Castle. The earliest departure is at 4:10 AM at night, and the last departure from Maidenhead is at 11:00 PM which arrives into Chepstow Castle at 6:44 AM. All services require a transfer at Reading and take an average of 2h 47m. The schedules shown below are for the next available departures.


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2h 20m • 2 changesWant to know about travelling from Maidenhead to Chepstow Castle? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.
No, there is no direct train from Maidenhead to Chepstow Castle. However, there are services departing from Reading station and arriving at Newport (S Wales) station via Newport (S Wales) station. The journey, including transfers, takes approximately 2h 47m.
Maidenhead to Chepstow Castle train services, operated by Great Western Railway (GWR), depart from Reading station.
Maidenhead to Chepstow Castle train services, operated by Great Western Railway (GWR), arrive at Newport (S Wales) station.
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The distance between Maidenhead and Chepstow Castle is 135.8 km. The road distance is 161 km.
Great Western Railway (GWR) operates a train from Reading to Newport (S Wales) hourly. Tickets cost £40–75 and the journey takes 1h 10m.