The average train between Middlesbrough and Chepstow takes 6h 4m and the fastest train takes 5h 18m. The train service runs several times per day 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 4 hours between Middlesbrough and Chepstow. The earliest departure is at 6:36 AM in the morning, and the last departure from Middlesbrough is at 7:25 PM which arrives into Chepstow at 6:47 AM. All services require a transfer at Darlington and take an average of 6h 4m. The schedules shown below are for the next available departures.


5h 18m • 2 changes


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5h 26m • 2 changes


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5h 27m • 2 changes


5h 26m • 2 changes


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5h 27m • 2 changes


5h 26m • 2 changes


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5h 27m • 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 Birmingham New Street. The journey, including transfers, takes approximately 6h 4m.
Middlesbrough to Chepstow train services, operated by Northern Trains Limited, depart from Darlington station.
Middlesbrough to Chepstow train services, operated by Northern Trains Limited, arrive at Chepstow station.
Book your Middlesbrough to Chepstow train tickets online with Northern Trains Limited and Cross Country.
The distance between Middlesbrough and Chepstow is 340.3 km. The road distance is 423 km.
You can take a train from Middlesbrough to Chepstow via Darlington and Birmingham New Street in around 5h 45m.