The average train between Middlesbrough and Chepstow takes 6h 23m and the fastest train takes 5h 22m. There is a train service every few hours from Middlesbrough 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 Middlesbrough and Chepstow. The earliest departure is at 6:17 AM in the morning, and the last departure from Middlesbrough is at 10:20 PM which arrives into Chepstow at 9:52 AM. All services require a transfer at Leeds and take an average of 6h 23m. The schedules shown below are for the next available departures.


5h 37m • 2 changes


5h 42m • 2 changes


6h 2m • 2 changes


5h 38m • 2 changes


5h 37m • 2 changes


5h 42m • 2 changes


6h 2m • 2 changes


5h 38m • 2 changes


5h 37m • 2 changes


5h 42m • 2 changes


6h 2m • 2 changes


5h 38m • 2 changes


5h 37m • 2 changes


5h 42m • 2 changes


6h 2m • 2 changes


5h 38m • 2 changes
Want to know about travelling from Middlesbrough 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 Middlesbrough to Chepstow. However, there are services departing from Middlesbrough station and arriving at Chepstow station via Leeds. The journey, including transfers, takes approximately 6h 23m.
Middlesbrough to Chepstow train services, operated by TransPennine Express, depart from Middlesbrough station.
Middlesbrough to Chepstow train services, operated by TransPennine Express, arrive at Chepstow station.
Book your Middlesbrough to Chepstow train tickets online with TransPennine Express, Cross Country and Transport for Wales.
The distance between Middlesbrough and Chepstow is 340.3 km. The road distance is 433 km.
You can take a train from Middlesbrough to Chepstow via Leeds and Cheltenham Spa in around 5h 58m.