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Trains from Winchelsea to
Chepstow

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Winchelsea to Chepstow by train

Considering a train trip from Winchelsea to Chepstow? The journey typically lasts around 5hrs 38 mins and spans about 153 miles (247 kilometres). With approximately 17 trains running each day, you're spoiled for choice when scheduling your travel. By booking your tickets in advance, you could secure fares starting from just £24.00, making it a budget-friendly option for smart travelers.

Winchelsea to Chepstow Key Stats

Arrival Station

Chepstow

Departure Station

Winchelsea

Frequency

17trains
per day

Journey Time

from4hrs 3 mins

Changes

4-4no direct
trains

First Train / Last Train

05:39 / 00:11

Distance

153miles
(247 km)

2 Routes

5 Train Operators

Prices

from£24.00

Travelling from Winchelsea to Chepstow by Train

Embark on a train journey from Winchelsea to Chepstow, and you'll find it's quicker than you might anticipate!

The typical travel time is about 5hrs 38 mins, but if you're in a hurry or just eager to arrive, the fastest trains can whisk you there in just 4hrs 3 mins. With approximately 17 trains running daily, you have a wealth of options to choose from. This scenic route, spanning 153 miles (247 km), generally involves just one transfer, and operators like GWR, CrossCountry, Southern, Southeastern, Transport for Wales offer comfortable seating with plenty of room for your luggage.

Here's the best part: by booking your tickets in advance, you can snag fares starting from only £24.00, offering a substantial saving over buying tickets at the last minute. For even more savings, consider traveling during Off-Peak times or using a Railcard.

Ready to secure those budget-friendly tickets? Use our Journey Planner to discover the latest deals and keep your travel costs down. Dive into more travel tips below or consult our timetable for up-to-date train schedules. All aboard for Chepstow!

Journey Details

Frequently asked questions about journeys between Winchelsea and Chepstow

Curious about your trip from Winchelsea to Chepstow? We've put together answers to the most commonly asked questions from our customers to make planning your journey easier.

How long does it take to travel between Winchelsea and Chepstow by train?

The travel time between Winchelsea and Chepstow by train varies depending on the type of train and the route, but the average journey time is 5hrs 38 mins & the fastest journey takes 4hrs 3 mins.

What's the fastest journey time between Winchelsea and Chepstow by train?

The fastest journey time by train from Winchelsea to Chepstow is 4hrs 3 mins.

How much does the train from Winchelsea to Chepstow cost?

Train ticket prices from Winchelsea to Chepstow can start from as little as £24.00 when you book in advance. The cost of tickets can vary depending on the time of day, route and class you book and are usually more expensive if you book on the day.

What are the departure and arrival times for trains between Winchelsea and Chepstow?

The departure and arrival times for trains between Winchelsea and Chepstow vary depending on the day of the week and the type of train. Generally, there are around 17 departures and arrivals throughout the day. The first departure is 05:39, and the last train of the day leaves at 00:11.

What is the difference between first class and standard class on trains between Winchelsea and Chepstow?

First class tickets on trains between Winchelsea and Chepstow typically offer more space, complimentary food and drink, and other amenities compared to standard class.

What amenities are available on trains between Winchelsea and Chepstow?

Amenities on trains between Winchelsea and Chepstow can include free Wi-Fi, power outlets, onboard catering, and comfortable seating.

What is the cheapest way to travel from Winchelsea to Chepstow by train?

By booking your tickets on traintickets.com! There are many ways to save on the cost of train travel between Winchelsea and Chepstow. On traintickets.com, we do all the work for you to find the cheapest way possible to get to Chepstow, and can save you up to 90%! Simply search for your journey, and be assured we have found you the best possible price.

Is it possible to take a direct train from Winchelsea to Chepstow?

No, unfortunately there are no direct trains between Winchelsea & Chepstow. However, there are 17 possible journeys which require a change.

What train companies run services from Winchelsea to Chepstow?

GWR, CrossCountry, Southern, Southeastern and Transport for Wales are the main train operating companies running services between Winchelsea and Chepstow.

Can I bring luggage on board trains between Winchelsea and Chepstow?

Yes, you can bring luggage on board trains between Winchelsea and Chepstow, but there may be limits on the number of bags or the size and weight of your luggage.

When are Winchelsea to Chepstow Train Times?

Check out the upcoming trains from Winchelsea to Chepstow on Friday 2nd May 2025, with our handy timetable below.

Alternatively, you can view the full day's schedule or search for a different date here!

Friday 2nd May
DepartsArrivesChangesVia StationsDurationOperator
07:39 Winchelsea12:16 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 37 mins Get Tickets
08:43 Winchelsea13:16 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 33 mins Get Tickets
09:43 Winchelsea14:45 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
5 hrs 2 mins Get Tickets
10:43 Winchelsea15:16 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 33 mins Get Tickets
11:43 Winchelsea15:46 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 3 mins Get Tickets
12:43 Winchelsea17:47 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
5 hrs 4 mins Get Tickets
13:43 Winchelsea18:16 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 33 mins Get Tickets
14:43 Winchelsea19:17 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 34 mins Get Tickets
15:43 Winchelsea20:25 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 42 mins Get Tickets
16:43 Winchelsea21:45 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
5 hrs 2 mins Get Tickets
17:43 Winchelsea22:20 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 37 mins Get Tickets
19:43 Winchelsea00:30 Chepstow4 changesAshford International
London St Pancras International
London Paddington
Newport (South Wales)
4 hrs 47 mins Get Tickets
Search all times & prices for today

What are my cheap ticket options for Winchelsea to Chepstow journeys?

From booking in Advance, to our FairSplits, here are our tips for you to find the best price

Advance Tickets

A single ticket for one journey leaving at a specific date and time.

The rule is: the sooner you book the cheaper they are. Usually the cheapest, but least flexible.

Advance fares from Winchelsea to Chepstow start from as little as £24.00

Off-Peak & Super Off-Peak Tickets

Offering greater flexibility than Advances, Off-Peak tickets offer travel during less busy times of day trading off more flexibility in the Off-Peak windows but for still discounted fares.

Off Peak fares from Winchelsea to Chepstow start from £88.40 one way, or £89.40 return

Anytime Tickets

Anytime tickets are fully flexible allowing travel at any time of the day. Brilliant if you don’t want the pressure of clock watching, returning when you want

Anytime fares from Winchelsea to Chepstow are available for £92.40 one way, or £299.00 return

With our FairSplit technology, you can save up to 90% on the cost of train travel.

Split ticketing means that instead of purchasing one rail ticket for your journey we automatically find and help you book two or more tickets instead, covering exactly the same journey. We call it our FairSplit.

Travelling in a group? We can save you even more!

Unlike other split ticketing sites, you can enter multiple railcards in a single search on traintickets.com. We will find you the best price using all possible combinations of your railcards in conjunction with our split ticketing technology & GroupSave.

When you do a search on traintickets.com we check all the cheapest prices automatically

Everything you need to know about Winchelsea Station

Welcome to Winchelsea Station

Winchelsea train station is a quaint little stop in the picturesque village of Winchelsea, East Sussex. Known for its charming rural setting, this station offers a peaceful starting point for travelers exploring the idyllic English countryside. While somewhat limited in size and amenities, Winchelsea station provides a unique charm that mirrors the captivating landscape surrounding it.

Facilities at Winchelsea Station

Though small, Winchelsea station provides essential facilities to ensure a smooth journey. Although there is no ticket office, travelers can buy or collect their tickets from the ticket machines available at the station. These machines are designed to be accessible, supporting transactions with Disabled Persons Railcard discounts. If you need assistance, help points are stationed around the platform, ensuring you are never far from help. While there's no formal waiting room, a seating area is available for the comfort of passengers.

The station's accessibility features include step-free access in certain areas, although some may find the steep ramp a challenge. If you require further assistance, you can use the staff-operated ramp to board trains, facilitated by train staff or pre-booked services. Be aware there are no dedicated staff for assistance traditionally available at the station, so planning ahead is beneficial.

Onward Travel Options

Winchelsea might not boast extensive transport connections, but it provides basic links to guide your onward journey. Various information resources, such as the Onward Travel Information Map, are available to assist with planning. Bus services and a rail replacement service are also connected, offering flexible options for continued travel. While there's no cycle hire or plentiful bicycle storage, the rural setting makes it perfect for serene walks as you explore East Sussex.

Embark on New Adventures from Winchelsea

If you're in search of destinations from Winchelsea station, exciting opportunities abound. Consider heading towards historical Hastings with its rich heritage, or the vibrant cityscape of London St Pancras International. Beach lovers might choose the coastal allure of Eastbourne, while cultural enthusiasts can visit the charming town of Rye. With well-timed connections, the world – or at least a stunning part of the UK – is effortlessly at your fingertips.

An Authentic Rural Experience

Before you leave, let Winchelsea station and its locale offer you an authentic taste of the English countryside, uninterrupted by the hustle and bustle of larger stations. Its simplicity is part of its charm, providing an undemanding starting point for your exploration. Whether you're a local making a daily commute or an adventurer setting off to see more of what Sussex and beyond has to offer, Winchelsea promises a gentle entryway into your journey.

As you plan your trip, remember to check for any service updates, especially if accessibility is a concern. Winchelsea may be small, but with a little planning, it serves as a delightful and strategic point of travel. Explore the ample opportunities for discovery ready for you, easily reachable by rail from Winchelsea.

Everything you need to know about Chepstow Station

Welcome to Chepstow Train Station

Chepstow, a charming town steeped in history and natural beauty, is home to a train station that is not only a gateway to Welsh landscapes but also a portal to explore various parts of the UK. Whether you're a resident or a visitor, the station offers the essential amenities and transport links necessary to make your journey smooth and enjoyable. Let's dive into what Chepstow train station has in store for you.

Station Amenities and Facilities

Chepstow station is equipped to handle a variety of commuter needs. If you're purchasing tickets, the station's ticket office is open from 06:30 to 17:30 on weekdays and from 08:00 to 13:00 on Saturdays. There are ticket machines available for those who prefer to collect tickets bought online or use a debit or credit card. For hearing-impaired passengers, an induction loop is provided.

The station provides step-free access to Platform 1, making it more accessible for travelers heading towards Gloucester. However, Platform 2 requires access via a footbridge, underlining the need for some passengers to plan accordingly.

While amenities such as waiting rooms and accessible toilets are not present, a café at the station ensures that you won't go hungry while waiting for your train. The station car park, managed by Transport for Wales, is open 24/7 and offers a small number of free parking spaces.

Transport Links and Options

The station offers convenient transport options for onward travel. There is a taxi rank located outside the front of the station for immediate travel needs. The rail replacement services, when required, operate from within the station car park. Although there are no bicycle hire facilities on-site, the town itself offers scenic routes for cyclists.

Popular Routes from Chepstow

From Chepstow, you can easily journey to a range of vibrant destinations. Whether it's a quick trip to Cardiff Central for some urban exploration or a longer trip to London Paddington for a taste of the cosmopolitan lifestyle, Chepstow station supports a variety of routes. Other popular destinations include Bristol Temple Meads, known for its historic architecture, and Cheltenham Spa, famous for its Regency buildings.

Planning Your Next Adventure

Looking to explore more of the UK by train? Chepstow is an excellent starting point. Consider venturing to cities like Birmingham or even a relaxing escape to the calming landscapes around Swansea. With great connections and convenient ticket purchasing options, your next journey is just a train ride away.

In conclusion, Chepstow train station, while maintaining a simpler set of amenities, acts as a hub to thriving Welsh towns and larger cities across the UK. Embrace the charm of train travel, purchase your tickets, and make the most of your journey from this quaint corner of Wales.

Looking for more inspiration?

Popular places to travel by train from Winchelsea