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Southend-on-Sea to Chepstow trains

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Trip Overview

The average train between Southend-on-Sea and Chepstow takes 4h 18m and the fastest train takes 3h 15m. There is a train service every few hours from Southend-on-Sea 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.

4h 18m
Duration
196 mi
Distance
£103
Average price
Hourly
Frequency

Train

best
  1. Take the train from Southend Victoria to Stratford (London)train train Southend Victoria - London Liverpool Street
  2. Take the train from London Paddington to Newport (S Wales)train train London Paddington - Swansea / ...
4h 2m
£84–153

Southend-on-Sea to Chepstow train times

Trains run hourly between Southend-on-Sea and Chepstow. The earliest departure is at 5:40 AM in the morning, and the last departure from Southend-on-Sea is at 11:01 PM which arrives into Chepstow at 8:15 AM. All services require a transfer at Stratford and take an average of 4h 18m. The schedules shown below are for the next available departures.

Departing Tuesday, October 13, 2026

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Transport for Wales3h 33m • 3 changes

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    Arrives next day

    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Transport for Wales3h 51m • 3 changes

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    Arrives next day

    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Transport for Wales9h 15m • 3 changes

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    Arrives next day

    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country9h 14m • 3 changes

Departing Wednesday, October 14, 2026

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 36m • 3 changes

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 21m • 3 changes

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Transport for Wales4h 1m • 3 changes

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 25m • 3 changes
  • Show more

Departing Thursday, October 15, 2026

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 36m • 3 changes

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 21m • 3 changes

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Transport for Wales4h 1m • 3 changes

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    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 25m • 3 changes
  • Show more

Departing Friday, October 16, 2026

  •  → 

    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 36m • 3 changes

  •  → 

    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 21m • 3 changes

  •  → 

    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Transport for Wales4h 1m • 3 changes

  •  → 

    Greater AngliaElizabeth Line (TfL)Great Western Railway (GWR)Cross Country3h 25m • 3 changes
  • Show more

Frequently asked questions

Want to know about travelling from Southend-on-Sea 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 Southend-on-Sea to Chepstow.ExpandLaunch map view
  • Distance: 195.6 mi
  • Duration: 4h 18m

What companies run services between Southend-on-Sea, England and Chepstow, Wales?

You can take a train from Southend Victoria to Chepstow via Stratford, London Paddington, and Newport (S Wales) in around 4h 2m.

Operators