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Middlesbrough to Chepstow trains

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Trip Overview

The train between Middlesbrough and Chepstow takes 5h 20m. The train runs, on average, 5 times per week 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.

5h 20m
Duration
267 mi
Distance
£126
Average price
5 times a week
Frequency

Middlesbrough to Chepstow train times

Trains run 5 times a week between Middlesbrough and Chepstow. The service departs Middlesbrough at 2:14 PM in the afternoon, which arrives into Chepstow at 19:34:00. All services require a transfer, and take on average 5h 20m. The schedules shown below are for the next available departures.

Departing Tuesday, October 27, 2026

  •  → 

    TransPennine ExpressCross Country5h 20m • 1 change

Departing Wednesday, October 28, 2026

  •  → 

    TransPennine ExpressCross Country5h 20m • 1 change

Departing Thursday, October 29, 2026

  •  → 

    TransPennine ExpressCross Country5h 20m • 1 change

Departing Friday, October 30, 2026

  •  → 

    TransPennine ExpressCross Country5h 20m • 1 change

Departing Monday, November 2, 2026

  •  → 

    TransPennine ExpressCross Country5h 20m • 1 change

Frequently asked questions

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.

Map of how to get from Middlesbrough to Chepstow.ExpandLaunch map view
  • Distance: 267 mi
  • Duration: 5h 20m

What companies run services between Middlesbrough, England and Chepstow, Wales?

You can take a train from Middlesbrough to Chepstow via Leeds in around 5h 48m.

Operators