The average train between Chepstow and Maidstone takes 4h 31m 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 8:24 PM which arrives into Maidstone at 12:35 AM. All services require a transfer at Gloucester and take an average of 4h 31m. The schedules shown below are for the next available departures.



4h 17m • 3 changes



3h 44m • 3 changes



3h 45m • 3 changes



3h 45m • 3 changes



9h 13m • 3 changes



4h 17m • 3 changes



3h 44m • 3 changes



3h 45m • 3 changes



9h 13m • 3 changes



4h 17m • 3 changes



3h 44m • 3 changes



3h 45m • 3 changes



9h 13m • 3 changes



4h 17m • 3 changes



3h 44m • 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 31m.
Chepstow to Maidstone train services, operated by Cross Country, depart from Chepstow station.
Chepstow to Maidstone train services, operated by Cross Country, arrive at Maidstone East station.
Book your Chepstow to Maidstone train tickets online with Cross Country, 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 52m.