The average train between Winchester and Chepstow takes 2h 43m and the fastest train takes 2h 13m. There is a train service every few hours from Winchester 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 every 2 hours between Winchester and Chepstow. The earliest departure is at 6:33 AM in the morning, and the last departure from Winchester is at 8:33 PM which arrives into Chepstow at 12:22 AM. All services require a transfer at Reading and take an average of 2h 43m. The schedules shown below are for the next available departures.


2h 15m • 2 changes


2h 43m • 2 changes


2h 13m • 2 changes


2h 15m • 2 changes


2h 42m • 2 changes


2h 44m • 2 changes


3h 13m • 2 changes


2h 42m • 2 changes


2h 42m • 2 changes


2h 44m • 2 changes


3h 13m • 2 changes


2h 42m • 2 changes


2h 42m • 2 changes


2h 44m • 2 changes


3h 13m • 2 changes


2h 42m • 2 changes
Want to know about travelling from Winchester 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 Winchester to Chepstow. However, there are services departing from Winchester station and arriving at Chepstow station via Reading. The journey, including transfers, takes approximately 2h 43m.
Winchester to Chepstow train services, operated by Cross Country, depart from Winchester station.
Winchester to Chepstow train services, operated by Cross Country, arrive at Newport (S Wales) station.
Book your Winchester to Chepstow train tickets online with Cross Country, Great Western Railway (GWR) and Transport for Wales.
The distance between Winchester and Chepstow is 114 km. The road distance is 239 km.
You can take a train from Winchester to Chepstow via Reading and Newport (S Wales) in around 3h 3m.