Windsor to Chepstow Trains

Windsor to Chepstow trains

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Trip Overview

The average train between Windsor and Chepstow takes 3h 35m and the fastest train takes 2h 35m. There is a train service every few hours from Windsor 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.

3h 35m
Duration: 134 mi
Distance: £77
Average price: Hourly
Frequency

Train

best

Take the train from Slough to Readingtrain Elizabeth / ...
Take the train from Reading to Newport (S Wales)train London Paddington - Swansea / ...

2h 57m

£55–126

Windsor to Chepstow train times

Trains run hourly between Windsor and Chepstow. The earliest departure is at 6:40 AM in the morning, and the last departure from Windsor is at 11:56 PM which arrives into Chepstow at 8:15 AM. All services require a transfer at Slough and take an average of 3h 35m. The schedules shown below are for the next available departures.

Departing Tuesday, August 18, 2026

7:00 PM → 9:44 PM
2h 44m • 3 changes
9:00 PM → 12:22 AM
Arrives next day
3h 22m • 3 changes
10:40 PM → 6:44 AM
Arrives next day
8h 4m • 3 changes
11:56 PM → 8:15 AM
Arrives next day
8h 19m • 3 changes

Departing Wednesday, August 19, 2026

6:40 AM → 9:16 AM
2h 36m • 3 changes
7:40 AM → 10:15 AM
2h 35m • 3 changes
9:00 AM → 11:44 AM
2h 44m • 3 changes
9:40 AM → 12:15 PM
2h 35m • 3 changes
Show more

Departing Thursday, August 20, 2026

6:40 AM → 9:16 AM
2h 36m • 3 changes
7:40 AM → 10:15 AM
2h 35m • 3 changes
9:00 AM → 11:44 AM
2h 44m • 3 changes
9:40 AM → 12:15 PM
2h 35m • 3 changes
Show more

Departing Friday, August 21, 2026

6:40 AM → 9:16 AM
2h 36m • 3 changes
7:40 AM → 10:15 AM
2h 35m • 3 changes
9:00 AM → 11:44 AM
2h 44m • 3 changes
9:40 AM → 12:15 PM
2h 35m • 3 changes
Show more

Frequently asked questions

Want to know about travelling from Windsor 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.