Top Things To Do In Chepstow: A Local’s Guide

Nestled on the banks of the River Wye, the historic town of Chepstow in Wales is a hidden gem waiting to be discovered. With its rich history, pretty landscapes, and vibrant culture, Chepstow offers an array of delightful experiences for travellers. Whether you’re a history buff, nature lover, or simply seeking a tranquil getaway, this town has something to offer everyone.

Having lived in Chepstow for the past six months, I wanted to put together this guide to the best things to do in this pretty little market town.

Pretty Chepstow town centre

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Exploring Chepstow

Situated in the lower Wye Valley, Chepstow or Cas-Gwent as it is known in Welsh, is a town that sits next to the Wye River, near the Severn Estuary. As the easternmost town in south Wales, Chepstow is known as the gateway to Wales.

The charming historical town centre is lined with quirky independent shops, cafes, colourful houses reminiscent of those in the Welsh seaside town of Tenby and topped off with lots of bunting! The large stone fortress of Chepstow Castle stands high over the River Wye, an impressive tidal river which was pivotal is securing Chepstow an important port throughout the ages.

As well as historical sites to visit, Chepstow also has an abundance of beautiful walks to enjoy, being the start/finish location of the Wales Coastal Path, the Offa’s Dyke Path, the Gloucestershire Way and the Monmouthshire Way.

Finally, this border town is also the location of Chepstow Racecourse which hosts the Welsh Grand National as well several festivals and events. So, let’s discover all the top things to do in Chepstow.

The 17 Best Things To Do In Chepstow

1. Explore Chepstow Castle

Embark on a journey through time at Chepstow Castle, one of the oldest surviving stone fortresses in Britain and one of the best castles in Wales. Built in the 11th century, this medieval stronghold boasts remarkable architecture, imposing towers, and stunning views of the River Wye.

Explore the castle’s nooks and crannies, stroll along the battlements, and soak in the grandeur of the Great Hall. The castle regularly hosts events and exhibitions, providing visitors with a captivating glimpse into its fascinating past.

Click here for the latest prices and opening hours.

2. Wye Valley Walk

Lace up your hiking boots and embark on an adventure along the Wye Valley Walk. This picturesque trail follows the course of the River Wye, offering breathtaking views of the surrounding countryside. Immerse yourself in nature as you meander through ancient woodlands, rolling hills, and charming riverside villages.

The Wye Valley Walk is perfect for both casual strolls and more challenging hikes, with sections catering to all fitness levels. Embarking on the whole walk would take around 10 days to complete. A lovely section to walk is from Chepstow to Tintern, which takes in the breathtaking views from Eagles Nest and is home to a carpet of bluebells and wild garlic in spring. The trail starts at Chepstow Castle and is accessed properly from Chepstow leisure centre.

3. Visit Chepstow Museum

Uncover Chepstow’s fascinating history at the Chepstow Museum. Housed in a charming 18th-century townhouse, the museum showcases a diverse collection of artefacts, photographs, and exhibits that chronicle the town’s past from its Roman origins through to its industrial heritage.

The museum also offers temporary exhibitions and educational programs, making it an enriching experience for all ages. Chepstow Museum is free to visit and is open every day except Wednesdays.

4. Enjoy the Sunday Market

Chepstow is an old English name meaning Market Town. Thankfully this historic tradition hasn’t disappeared as Chepstow still hosts a local market. 

Every fourth Sunday of the month, Chepstow High Street is overtaken by local vendors who come to ply their wares. Stalls here sell everything from candles and jewellery to patisseries and international cuisines. The market runs from 11am to 3pm and is a great addition to your Chepstow itinerary.

5. Explore Tintern Abbey

Just a short drive from Chepstow lies the mesmerising ruins of Tintern Abbey. Founded in 1131, this Cistercian monastery is a testament to Gothic architecture and a source of inspiration for poets like William Wordsworth and artists such as JMW Turner.

Wander through the abbey’s majestic ruins, marvel at the intricate stonework, and feel the weight of history as you soak in the tranquil atmosphere. Don’t forget to capture the ethereal beauty of the abbey framed against the backdrop of the lush Wye Valley.

Located just 6 miles from Chepstow, Tintern Abbey is accessible by bus, car, bike or on foot. You can see the latest prices here.

6. Walk the Wales Coast Path

For those seeking fresh air and stunning landscapes, the Wales Coast Path is a true gem. Chepstow marks the start/finish point of this long-distance trail that spans over 870 miles, following the country’s entire coastline. Take a leisurely walk along the path, relishing the panoramic views of the river, cliffs, and lush countryside.

The start/finish point can be found in Riverside Park in an area known as The Back, meaning wharf, as this was previously an important port area with shipyards and docks. Across the river you will see Gloucester Hole, which is a man-made cave dating back to the industrial era and, if you’re lucky, you may spot peregrines that live on the surrounding cliffs.

7. Enjoy High Tea at the Beaufort Hotel

The Beaufort Hotel was previously a Coaching Inn and continues to offer accommodation to travellers visiting Chepstow. The bar is a popular watering hole for locals and the restaurant serves award winning food.

However, the courtyard is a delightful location to enjoy a cream tea. The chefs here make some seriously tasty scones which are best enjoyed with lashings of cream and jam, and washed down with a pot of tea.

8. Visit Chepstow Racecourse

If you’re a fan of horse racing, a visit to Chepstow Racecourse is a must. Set against the backdrop of the beautiful Wye Valley, this premier racecourse hosts thrilling races throughout the year. Experience the excitement as the horses thunder down the track, place a bet, and soak in the lively atmosphere of the racecourse.

The racecourse also hosts music and performance events at various points throughout the summer, so if you’re able to plan your trip to Chepstow on one of these dates you’ll all be set for an amazing time. This summer has seen musical performances from Lionel Richie and George Ezra as well as the Chepstow Show, which includes the Welsh Axemen and Paws for Thought Dog Display Team.

You can buy tickets for musical events at Chepstow on Ticketmaster.

George Ezra at the Racecourse

9. Shop and Dine in the Town Centre

Chepstow’s town centre is a delight for shopaholics and food enthusiasts alike. Explore the charming streets lined with independent boutiques, antique shops, and art galleries, where you can find unique souvenirs and local crafts. Check out Chepstow Records if you’re a fan of vinyl records, visit Kreations for unique gifts and wander Captivate for local photography prints.

After a day of shopping, treat yourself to a meal at one of the town’s delightful eateries, offering a variety of cuisines from traditional Welsh fare to international delicacies. There is award-winning pizza at Stone Rock Pizza, top Greek dishes at Mythos Meze, delicious Indian food at the Mango House, quality Italian dishes at Una Vita and locally sourced pub fare at the Riverside Restaurant.

10. Admire the Old Wye Bridge

After it’s completion in July 1816, Chepstow Bridge was was the world’s largest iron arch bridge. This architectural marvel and feat of engineering has stood the test of time and is best viewed from the Riverside park, a short walk from Chepstow Castle.

Crossing the Wye river over the Old Wye Bridge transports visitors from Wales into England. If you stand in the centre of the bridge you can have one foot in each country! During high tide, seals often travel up the river to feed and the bridge offers the perfect vantage point to watch these delightful animals as they fish.

The Old Wye Bridge is an important site in Chepstow

11. Kick back at a coffee shop

There is certainly no shortage of coffee shops and cafes in Chepstow. Independent cafes include the Cwtch (a Welsh word meaning hug) which is tucked away in an alley off Bank Street, Ugly Mug situated on the main High Street and Marmalade House Vintage Tea Room for something a bit special.

12. Visit St Mary’s Priory

A short distance from Chepstow castle is St Mary’s Priory. The Priory was built just a few years after the castle but the only part of the priory that now dates back to that era is the nave. The rest of the priory fell into ruin after the dissolution of King Henry VIII and most of what can be seen today dates back to the Victorian era.

The church is open to visitors daily from 10am-4pm and welcomes donations. The churchyard is also worth exploring as it has become a rewinding project, making it a sanctuary for wild flowers and wildlife.

St Mary's Priory is an important historical site in Chepstow and a popular place to visit

13. Take a Boat Trip on the River Wye

Discover the magic of the River Wye by embarking on a boat trip. Cruise along its meandering waters, bask in the serenity of the surroundings, and keep an eye out for wildlife, including herons, kingfishers, and seals.

Whether you opt for a relaxing sightseeing cruise or an adventurous canoe trip, exploring the river is an excellent way to connect with nature and appreciate the idyllic charm of the area.

Wye Valley Cruises offer daily cruises for less than £10 and Canoe the Wye offer half day canoe hire for £60. Both operate from Symonds Yat which is a little further up the Wye Valley from Chepstow.

Canoeing the Wye is a fun thing to do in Chepstow

14. Attend Chepstow Festivals and Events

Throughout the year, Chepstow hosts a variety of festivals and events that showcase the town’s vibrant culture. From music festivals to food fairs, there’s always something interesting happening in Chepstow.

The bandstand at The Back is often the location for musical performances so pull up a camp chair and enjoy the free shows. Nearby Tintern is also home to an annual Folk Festival and Chepstow Castle hosts a variety of musical artists and plays.

Check the local event calendar and plan your visit accordingly to join in the festivities or if you’re already in town, visit the Chepstow Tourist Information Centre for all the latest information.

15. Enjoy a Local Walking Loop

As a Walkers Are Welcome town, Chepstow is home to many beautiful walks with guided walks taking place on most days through the summer. If you prefer to explore by yourself, here are a few of my favourite trails.

The Eagle’s Nest Trail starts from either Upper Wyndcliff, which has a height barrier so isn’t suitable for motorhomes or camper vans, or from Lower Wyndcliff car park. The loop is 2km and visits the Eagle’s Nest Viewpoint which is a vista that stretches over the lower Wye Valley and out to the Severn Estuary. To complete the loop, take on the 365 steps that descend through an atmospheric forest and back to the start.

The Devil’s Pulpit loop from Tintern Abbey walks a section of another long distance trail known as  Offas’s Dyke. The walk begins by crossing the bridge at Tintern, before climbing up through the woods to Offa’s Dyke path and along to the intriguing Devil’s Pulpit Viewpoint. After admiring distant views of Tintern Abbey, continue along the path as it descends down into the valley and loops back around to the bridge at the edge of Tintern town.

Lancaut and Ban-y-Gor nature reserve is a quieter walk around Chepstow which again offers fabulous views over the Wye River. From the car park on Lancaut Lane, follow the footpath to the riverside, taking note of the lime kilns tucked away in the cliffs and stopping off to visit St James Church en-route. A boulder scree offers an interesting scramble to get back up to the cliff top, before admiring the views and interesting legend at Wintour’s Leap.

16. Immerse Yourself in History at Chepstow Town Gate

The Chepstow Town Gate is a well-preserved historical landmark that provides a glimpse into the town’s past. Walk through the gate and explore the narrow streets of Chepstow, admiring the charming architecture and absorbing the ambiance of this ancient town. The old city wall can also be seen at several points around the town.

17. Enjoy the Local Music Scene

The Boat Inn, Riverside Restaurant and the Three Tuns have regular live music throughout the summer. The Boat and Riverside usually have solo artists who share their songs against the backdrop of the Wye river, whilst the Three Tuns host lively bands and a pop-up food stall which rotates through a selection of international cuisines. Weather permitting, the bandstand in Riverside Park also hosts musicians every Sunday throughout the summer. 

The pubs usually coordinate with each other so that the gigs don’t clash and visitors can enjoy live music all weekend. For those who want to share their musical talents, the Boat Inn also has an open mic night every Thursday night.

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Places To Stay In Chepstow

Chepstow has a small selection of accommodation options to suit all visitors. Here are my top picks.

No8 Chepstow is a terrace house that has three rooms available to rent. The rooms are modernly furnished and there is access to a shared lounge, kitchen and garden. The house is perfectly placed so that all attractions are within walking distance.

Alternatively, for something with a little more age and character, try The Three Tuns. This cosy pub is over 400 years old and is centrally located next to the castle.

If you’re using Chepstow as a base to explore other parts of South Wales then try the Two Rivers Lodge. This modern accommodation is located 1 mile from the historic centre but is perfectly placed for quick access the motorways.

How To Get To Chepstow


Trains run from Cardiff to Chepstow every hour and take around 30 minutes. Hourly trains running from London take around 2.5 hours. Easily book your train tickets here.


Chepstow is serviced by regular daily buses from London which take around 2 hours and the capital of Cardiff which takes around 45 minutes. You can pre-book bus tickets here.


Chepstow is closely positioned near the M4 motorway, making it easy to access from London, which is a 2 hour drive. Cardiff is a 40 minute drive away. There is a large pay and display car park situated next to the castle and several smaller car parks dotted around the town. 

For the best deals on car rentals I recommend Discover Cars.

Final Thoughts On Things To Do In Chepstow

Chepstow, with its historic treasures, natural wonders, and warm hospitality, promises an unforgettable experience for all who visit. From its commanding castle and serene river to its industrial heritage and charming town centre, this Welsh town is a destination that effortlessly blends the old and the new.

So, pack your bags, embark on a journey to Chepstow, and immerse yourself in the beauty and charm of this Welsh hidden gem.

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Louise is an Adventure Tour Guide, Snowboard Instructor & Mountain Leader from South Wales. Through working as a tour guide and snowboard instructor, she has spent the last 15 years travelling Asia, Africa and the Americas. Louise is a published photographer and currently guides mountain trips in the UK.

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