The average train between Maidenhead and Chepstow Castle takes 2h 44m and the fastest train takes 1h 49m. 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 44m. The schedules shown below are for the next available departures.


2h 12m • 2 changes


2h 14m • 2 changes


2h 32m • 2 changes


2h 24m • 2 changes


2h 19m • 2 changes


2h 18m • 2 changes


2h 48m • 2 changes


2h 43m • 2 changes


2h 40m • 2 changes


2h 7m • 2 changes


2h 8m • 2 changes


2h 9m • 2 changes


4h 5m • 2 changes


2h 5m • 2 changes


2h 3m • 2 changes


2h 20m • 2 changes
Want 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 Maidenhead station and arriving at Chepstow Castle station via Newport (S Wales). The journey, including transfers, takes approximately 2h 44m.
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.
Book your Maidenhead to Chepstow Castle train tickets online with Great Western Railway (GWR), Cross Country and 2 other operators.
The distance between Maidenhead and Chepstow Castle is 135.8 km. The road distance is 203 km.
Great Western Railway (GWR) operates a train from Reading to Newport (S Wales) hourly. Tickets cost £40–85 and the journey takes 1h 9m.