The average train between Windsor Castle and Chepstow takes 3h 29m and the fastest train takes 2h 52m. There is a train service every few hours from Windsor Castle to Chepstow. 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 Windsor Castle and Chepstow. The earliest departure is at 6:00 AM in the morning, and the last departure from Windsor Castle is at 9:00 PM which arrives into Chepstow at 6:16 AM. All services require a transfer at Windsor & Eton Central and take an average of 3h 29m. The schedules shown below are for the next available departures.



2h 52m • 3 changes



3h 16m • 3 changes



2h 52m • 3 changes



2h 52m • 3 changes



2h 53m • 3 changes



2h 52m • 3 changes



3h 16m • 3 changes



2h 54m • 3 changes



2h 53m • 3 changes



2h 52m • 3 changes



3h 16m • 3 changes



2h 54m • 3 changes



3h 2m • 3 changes



3h 16m • 3 changes



2h 53m • 3 changes



2h 52m • 3 changes
Want to know about travelling from Windsor Castle to Chepstow? 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 Windsor Castle to Chepstow. However, there are services departing from Windsor Castle station and arriving at Chepstow station via Gloucester. The journey, including transfers, takes approximately 3h 29m.
Windsor Castle to Chepstow train services, operated by Great Western Railway (GWR), depart from Reading station.
Windsor Castle to Chepstow train services, operated by Great Western Railway (GWR), arrive at Chepstow station.
Book your Windsor Castle to Chepstow train tickets online with Great Western Railway (GWR), Cross Country and 2 other operators.
The distance between Windsor Castle and Chepstow is 144.3 km. The road distance is 201 km.
You can take a vehicle from Windsor Castle to Chepstow via Windsor & Eton Central, Slough, Reading, and Gloucester in around 3h 46m.