How to spend 48 hours in Chepstow
Chepstow blends the very best of ancient and modern.
Border town Chepstow blends the best of ancient and modern, a major medieval powerhouse with its Norman castle strategically built along a limestone cliff overlooking the meandering River Wye. Known as 'the gateway of Wales', Chepstow derives from the old English 'chepe stowe', meaning a market place, and today the small, historic town retains its cobbled streets and has an impressive variety of independent shops, cafés, restaurants and pubs.
It's an underrated town in the lower Wye Valley that deserves a full weekend to make the most of the scenic hikes, shops, nearby attractions and independent restaurants.
What to do in Chepstow
You can't visit the town without seeing the impressive Chepstow Castle, Wales' oldest surviving post-Roman castle that dates back to 1067.
The town centre is also full of quirky gift shops and a few antique shops where you can hunt for treasures. There are also plenty of cafes and restaurants to discover.
Known for its horse racing, there is a wide range of other events held throughout the year at Chepstow Racecourse, home to the Coral Welsh Grand National.
There has been horse racing here since the late 19th century. St. Pierre Marriott Hotel & Country Club has one of the country's finest and most picturesque golf courses, and for many years was host to the British (formerly Dunlop) Masters tournament, which attracted some of the top players in the world.
Chepstow is also an outdoor adjacent gateway town that's perfect for hiking and gentle walks, with many long-distance trails starting here, including the Wye Valley Walk, the Offa's Dyke National Trail and the Wales Coast Path.
Hiking fans will love the Wye Valley walk between Chepstow and Tintern Abbey. Walk up ancient stone steps and through ethereal forest paths. There are Plenty of viewpoints where you can picnic and photograph the winding River Wye.
Here are some of the highlights and best things to do in and around Chepstow.
Explore Chepstow Castle
Chepstow Castle is a beautifully preserved Welsh castle that proudly stands atop a limestone cliff above the River Wye, having stood the test of time. It's a must-visit place when spending a weekend in Chepstow.
For more than six centuries, Chepstow was home to some of the wealthiest and most powerful men of the medieval and Tudor ages.
Building was started in 1067 by Earl William Fitz Osbern, a close friend of William the Conqueror, making it one of the first Norman strongholds in Wales. In turn, William Marshal (Earl of Pembroke), Roger Bigod (Earl of Norfolk) and Charles Somerset (Earl of Worcester) all made their mark before the castle declined after the Civil War.
The oldest building is the Norman great tower, but building work continued well into the 17th century as stronger musket-friendly parapets replaced medieval battlements.
Today, visitors can learn more about this historic site that Cadw now manages by visiting this impressive castle on a day trip or booking one of their special events. There's a range of facilities here, including a gift shop, bike access and parking. From superstar gigs to cosy pubs, find out What’s On in Wales by signing up to our newsletter here
Visit Chepstow Museum
Continuing your history education, you can learn more about Chepstow's many industries at the Chepstow museum, housed in an elegant 18th-century house built by a prosperous Chepstow merchant family.
Get an insight into Chepstow's wine trade, shipbuilding, and salmon fishing, which are featured in the museum's displays with atmospheric settings. In the Middle Ages, imported wine was offloaded on Chepstow's quayside.
Here, you'll find Photographs, programmes and posters recalling local people's pastimes, whilst 18th and 19th century paintings and prints illustrate the everlasting appeal of Chepstow and the Wye Valley to artists and tourists.
Paddleboard on the River Wye
The River Wye is a long and accessible river that flows through many villages and towns, including Chepstow. You'll find plenty of paddle spots and waterside pubs along the river, and it's also the perfect place to try paddleboarding.
Stand-up paddleboarding – or SUP – is an entertaining activity for all the family and is suitable for most ages and abilities.
You need to put a fair amount of effort into staying upright and balanced when you start. It's guaranteed you'll all fall in at some point, so perhaps take a waterproof camera to capture the most hilarious fails.
Gently paddling down the river is a unique way of experiencing the beautiful scenery of the Wye Valley, spotting wildlife, and getting a great core muscle workout.
Several companies in the area offer a range of SUP experiences for all ages, including the family-run Inspire2Adventure.
Do the Wye Valley Walk
Plenty of hiking routes and shorter walking trails can help you discover the beauty of the Wye Valley on foot. If you are looking for a longer walk in this area, opt for the Wye Valley Walk, a long-distance national trail that follows the course of the River Wye.
You can choose various sections of the trail for day hikes and weekend hikes, or opt for a full walking holiday and do the lot. One of the best day hikes on the Wye Valley Walk is the Chepstow to Tintern Abbey section.
It's a scenic, five-mile walk that takes you up ancient stone steps and through ethereal forest paths. There are plenty of photo and picnic spots along the way, and you'll also find some viewing points where you can gaze at the winding River Wye.
Autumn is the best time to attempt this trail: when the leaves change their colours, it becomes one of the prettiest hiking trails in the UK. Pack a picnic to round out the country experience.
Explore Tintern Abbey
One of our greatest monastic ruins, this is surely the best-preserved medieval abbey in Wales. Tintern Abbey is just a short drive from Chepstow, or you can walk from Chepstow to Tintern Abbey on the Wye Valley Walk.
It was founded in 1131 by Cistercian monks and has had a long history, including the dissolution of the monasteries, which led to the abbey slowly turning into a majestic ruin.
Today, you can visit this important heritage site in Wales and marvel at the scale of the roofless abbey and the British Gothic architecture. Tickets can be bought on arrival at the visitor centre, and a selection of guidebooks can help you learn more about this beautiful abbey.
Wander the forest trails in Puzzlewood
Just a 20-minute drive from Chepstow, you'll find the ethereal forest of 'Puzzlewood'. Situated just over the Welsh border, this 14-acre ancient woodland offers meandering pathways and fantastical trees and is home to badgers, deer, foxes, rabbits and bats.
The spellbinding forest landscape is so unique that Kathleen Kennedy, President of Lucasfilm (known for the legendary Star Wars and Indiana Jones franchises), has even declared it 'the most magical forest on the face of the earth!'
t's easy to see why Puzzlewood has been a favourite location for filmmakers. Its surreal landscapes provide the perfect backdrop for productions like Merlin, Star Wars, and The Secret Garden (2020).
The mysterious forest is known for being a key filming location for Star Wars: The Force Awakens (2015).
This ancient woodland was transformed into the lush, green forest world of Takodana, where pivotal scenes unfold. Among these is the dramatic lightsaber battle between Rey (Daisy Ridley) and Kylo Ren (Adam Driver).
Puzzlewood's natural, mystical atmosphere made it the perfect setting for this iconic scene. Star Wars location manager Martin Joy described the forest as 'like nowhere else, it's an otherworldly space'.
While Puzzlewood's natural beauty is undoubtedly its main draw, there's much more to discover beyond the twisting paths and ancient trees.
Scattered throughout the forest are a series of intriguing features, including bridges, lookouts, and even a few dead ends, that add an element of mystery to your exploration.
Puzzlewood is also home to various animals, making it a delightful family destination. Visitors can meet Highland cattle, donkeys, ducks, and chickens, turning a walk through the woods into a mini safari.
After exploring the forest, visitors can relax at the small takeaway café on site, which offers a range of refreshments.
Alternatively, you can bring your own picnic and find a quiet spot in the woods to enjoy your meal surrounded by nature.
Where to eat
Chepstow is ideally positioned in the surprising foodie hotspot The Wye Valley, where the lengthy River Severn meets the salmon-rich River Wye, carving through Wales and England.
Whilst this charming border area is known for its protected landscapes, ancient monuments, attractive market towns and outdoor pursuits, there's also a thriving dining and foodie scene to be discovered.
You can criss-cross seamlessly from Wales into England and easily explore the well-heeled area and its many restaurants, cafes and producers.
Take a gastro-journey through the valley and you'll find locally reared lamb, smoked eel, craft ales and honey-infused mead.
Local breweries include small microbrewery Lydbrook Valley Brewing Company, producing a 4.2% IPA and the Wye Valley Brewery, producing a decent range of craft ales.
The Wye Valley even has its vineyard in White Castle Vineyard, where visitors can buy Welsh wines and tour the small vineyard.
Numerous pubs along the River Wye are a welcome rest spot if you're paddling up the river on an epic canoe or kayak trip whilst visiting Chepstow. The Boat Inn and the Anchor Inn offer local ales and river views.
Numerous pubs along the River Wye are a welcome rest spot if you're paddling up the river on an epic canoe or kayak trip. The Boat Inn and the Anchor Inn offer local ales and river views.
One of the best spots for a pint by the water is the Saracens Head Inn. This historic, riverside inn has stood for centuries in its spectacular position on the east bank of the River Wye, where the river flows into a steep wooded gorge.
Here you'll find rooms, award-winning food and local ales. Their flagstone-floored bar and rustic pine tables provide a traditional pub feel as you sip on a pint of local real ale, watching the Inn's ancient hand ferry carry passengers across the Wye.
Over in the city centre, the Beaufort Hotel's award-winning restaurant offers guests a fabulous à la carte menu featuring traditional British and international dishes, using Wye Valley and Welsh produce where possible.
Tell me Wine is a wine merchant and French bistro lounge that offers delicious French dishes, wine tastings, and live music events. Family-owned Stone Rock Lodge serves Wales' best pizza, and you can get a banging Sunday lunch at St Pierre.
Where to stay
There is an impressive range of Airbnb properties, guest houses, and hotels in Chepstow and the wider area to suit your travel style and budget. Weekend Candy has a range of unique stays in the Wye Valley, from luxury Glamping and Yurts to cosy holiday cabins.
Delta Hotels by Marriott St Pierre Country Club is built around a beautiful 14th-century manor house, ideally located only a short drive from the Old Severn Bridge.
The Beauford hotel is a family-run and historic inn in the heart of Chepstow that is very reasonably priced. You'll also find excellent food (AA rosette) and a popular bar here.
Further afield is the charming Tudor Farmhouse, around a 20-minute drive from Chepstow. This boutique hotel is a former working farm that has been stylishly converted into a country getaway with rooms, cottages and suites. Prices depend on the type of room booked.
You should not miss the chance to dine at Tudor Farmhouse. Their head chef ensures that quality and locally-sourced ingredients are used in their seasonal dishes.
Farmhouse meets upscale dining here with flickering candles, exposed stone walls, and slightly hushed tones. This contrasts beautifully with the scent of homemade food wafting through the dining room.