What to do in Chepstow

Activities, attractions and tours

Tintern Abbey showing building ruins, heritage architecture and heritage elements
Tintern Abbey showing a ruin, heritage architecture and heritage elements
Tintern Abbey featuring building ruins, heritage elements and heritage architecture
Tintern Abbey showing heritage elements, building ruins and heritage architecture
Tintern Abbey showing heritage elements, heritage architecture and building ruins

Chepstow Attractions

Let Expedia help you to experience the best that Chepstow has to offer! If you’re planning a trip to Chepstow, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling to Chepstow with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Places of interest in Chepstow

Chepstow is crammed with must-see places to visit and things to do. We can help you decide where to stay in Chepstow, and make it a breeze to explore Chepstow and the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Chepstow to make sure that you enjoy your holiday to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit to Chepstow, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights in Chepstow.

Chepstow attractions

Chepstow has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions in Chepstow to keep you entertained. Expedia makes it easy to book your flight, hotel and rental car in advance, making for hassle-free travel and freeing you up to explore the sights of Chepstow.

Looking for things to do in Chepstow can be time-consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine of Chepstow or catch up with the vibrant local culture, our guides to Chepstow attractions ensure that you’ll have a successful trip, whatever the season. Happy trails!

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Most fun & popular experiences in Chepstow

Tours & day trips

See all 22 activities
Cocktail Lovers Masterclass

Cocktail Lovers Masterclass

Activity duration is 2 hours
10.0 out of 10 with 1 review
Free cancellation available
Price is £30 per adult
Cocktail Lovers MasterclassOpens in new tab

Food, drink & nightlife

See all 3 activities
Cocktail Lovers Masterclass

Cocktail Lovers Masterclass

Activity duration is 2 hours
10.0 out of 10 with 1 review
Free cancellation available
Price is £30 per adult
Cocktail Lovers MasterclassOpens in new tab

Classes & workshops

See all 3 activities
Cocktail Lovers Masterclass

Cocktail Lovers Masterclass

Activity duration is 2 hours
10.0 out of 10 with 1 review
Free cancellation available
Price is £30 per adult
Cocktail Lovers MasterclassOpens in new tab

What to do in Chepstow

Popular places to visit

Millennium Stadium featuring a river or creek and modern architecture

Principality Stadium

The spiritual home of Welsh rugby, the Principality Stadiumin Cardiff is one of the most famous sporting arenas on the planet, envied the world over for its cauldron-like atmosphere and state-of-the-art facilities.

Principality Stadium
Pierhead Building, a Grade One listed building of the National Assembly for Wales in Cardiff Bay, Wales. A Cardiff's landmark taken from Cardiff Bay.

Cardiff Bay

Explore the waterfront in Cardiff with a trip to Cardiff Bay. Discover the lively bars and acclaimed theatre scene in this relaxing area.

Cardiff Bay
Cardiff Castle showing heritage architecture, château or palace and heritage elements

Cardiff Castle

Located in the heart of the city centre, Cardiff Castle is one of Wales’ most important cultural attractions. A rich history spanning 2,000 years is contained within its walls and fairytale-style towers.

Cardiff Castle
Aerial panorama of Barry Island, Wales, UK

Barry Island Beach

If you’re looking for a quintessential Welsh seaside experience, look no further than Barry Beach in the picturesque Vale of Glamorgan.

Barry Island Beach
D6WYKM Aerial photograph of the Cardiff Motorpoint Arena

Utilita Arena Cardiff

Cardiff Motorpoint Arena is located on Mary Ann Street in the heart of Cardiff. It was opened in 1993 and is the largest purpose-built facility for staging exhibitions and concerts in South Wales.

Utilita Arena Cardiff
Main building of Cardiff University - Wales; Shutterstock ID 289260233; purchase_order: Comps; job: ; client: ; other:

Cardiff University

Founded by Royal Charter in 1883 and located in the heart of the thriving Welsh capital, Cardiff University has built an international reputation for the quality of its work.

Cardiff University
Wales Millennium Centre which includes modern architecture, street scenes and signage

Wales Millennium Centre

An architectural masterpiece, the Wales Millennium Centre is at the heart of Cardiff Bay, a wonderfully regenerated area full of striking buildings, wide open spaces and intriguing pieces of public art.

Wales Millennium Centre
Tintern Abbey featuring château or palace, a church or cathedral and religious elements

Tintern Abbey

The monastic ruins of Tintern Abbey are nestled in the heart of the Wye Valley area of outstanding natural beauty and can boast 900 years of history in their walls. This was the first Cistercian abbey built in Wales and only the second in Britain, and despite now being exposed to the elements, it remains one of the most stunning surviving examples of gothic architecture in the country.

Tintern Abbey
Cardiff Bay

Cardiff Bay Waterfront

Learn about the local history of Cardiff when you take a trip to Cardiff Bay Waterfront. Discover the area's entertainment choices or seek out its local tours.

Cardiff Bay Waterfront

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Day trip destinations from Chepstow

Wills Memorial Building which includes a city, heritage elements and night scenes

Bristol

Tintern Abbey

Tintern

View of Newport Sands Beach from the golf club. Newport, Pembrokeshire, Wales. UK

Newport

Monmouth Viaduct an old derelict railway viaduct bridge crossing the river Wye in Monmouthshire Wales.

Monmouth

The castle courtyard highlights some of the fine details that went into the castle construction. Raglan is a grand 15th-century castle that eventually fell to Parliamentary forces during the English Civil War (1646). The castle was surrendered mostly in-tact, but was slighted (purposefully disabled) to prevent any future use as a fortification. Today it's an atmospheric ruin that makes for a fun visit.

Usk

The harbour entrance at Lydney

Lydney

Cardiff which includes street scenes, a city and night scenes

Cardiff

The castle courtyard highlights some of the fine details that went into the castle construction. Raglan is a grand 15th-century castle that eventually fell to Parliamentary forces during the English Civil War (1646). The castle was surrendered mostly in-tact, but was slighted (purposefully disabled) to prevent any future use as a fortification. Today it's an atmospheric ruin that makes for a fun visit.

Raglan

Frequently asked questions

Is Chepstow worth visiting?
Chepstow offers a unique blend of local charm, attractions and culture. Whether you're into nature, history or regional cuisine, there's a lot here to enjoy.
How do I spend a day in Chepstow?
Start your sightseeing with a visit to Chepstow Castle and Caldicot Castle. Then, tour different parts of Chepstow for local dining and some shopping.
What is the top tourist attraction in Chepstow?
Chepstow Castle is one of the top tourist attractions in Chepstow and should feature high on every to-do list of the area.
Is three days enough to stay in Chepstow?
Three days will give you time to tick off many city sights, such as Chepstow Castle, Caldicot Castle and Symonds Yat Rock. The average stay in Chepstow is two days. If you have the time to extend your holiday, Bath isn't far away.
What are some activities to do in Chepstow with kids?
Deciding what to do in Chepstow with kids has never been easier. Whether you're taking a trip with toddlers or teenagers, there are loads of family-friendly tours and attractions to keep them busy here.

What to do in Chepstow for adults?
Whether you're a culture enthusiast, avid foodie or outdoor explorer, there are loads of things to do in Chepstow for adults including Parva Farm Vineyard.
Are there free things to do in Chepstow?
From enjoying parks to wandering around vibrant neighbourhoods, it's simple to discover free things to do in Chepstow. If you're in need of ideas, ask for tips from a local tour guide. Chepstow Museum is a must for anyone wanting to save on their travelling adventures.

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