The average train between Chepstow and Maidstone takes 4h 38m and the fastest train takes 3h 44m. There is a train service every few hours from Chepstow to Maidstone. 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 Chepstow and Maidstone. The earliest departure is at 12:23 AM at night, and the last departure from Chepstow is at 11:10 PM which arrives into Maidstone at 9:36 AM. All services require a transfer at Gloucester and take an average of 4h 38m. The schedules shown below are for the next available departures.



9h 12m • 3 changes



4h 17m • 3 changes



3h 44m • 3 changes



3h 45m • 3 changes



9h 12m • 3 changes



4h 17m • 3 changes



3h 44m • 3 changes



3h 45m • 3 changes



10h 1m • 3 changes



3h 45m • 3 changes



3h 45m • 3 changes



3h 44m • 3 changes
Arrives next day



23h 22m • 3 changes
Arrives next day



10h 26m • 3 changes



4h 17m • 3 changes



3h 44m • 3 changes



3h 45m • 3 changes



3h 45m • 3 changes
Want to know about travelling from Chepstow to Maidstone? 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 Chepstow to Maidstone. However, there are services departing from Chepstow station and arriving at Maidstone station via Gloucester. The journey, including transfers, takes approximately 4h 38m.
Chepstow to Maidstone train services, operated by Transport for Wales, depart from Chepstow station.
Chepstow to Maidstone train services, operated by Transport for Wales, arrive at Maidstone East station.
Book your Chepstow to Maidstone train tickets online with Transport for Wales, Great Western Railway (GWR) and 3 other operators.
The distance between Chepstow and Maidstone is 225.1 km. The road distance is 293 km.
You can take a train from Chepstow to Maidstone East via Gloucester, London Paddington, Paddington station, Charing Cross station, and London Charing Cross in around 4h 56m.